Imidazo[1,2-a]pyrimidine and fungicidal compositions containing thereof

ABSTRACT

The imidazo[1,2-a]pyrimidines given by the following formula [I]: 
                         
[wherein R 1  and R 2  represent a C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; or R 1  and R 2  represent a 3–8 membered heterocyclic group together with the nitrogen atom bonded with R 1  and R 2 ; R 3  represents a halogen atom or C1–C4 alkyl group; and Ar represents a phenyl group optionally substituted by a halogen atom or atoms; and the like] have excellent activity for controlling plant diseases.

TECHNICAL FIELD

The present invention relates to imidazo[1,2-a]pyrimidine and fungicidal composition containing thereof.

BACKGROUND ART

Japan unexamined patent application 2001-19693 discloses pyrazolo[1,5-a]pyrimidines given by the following formula:

[wherein Z represents O, S, NA² or a single bond; A¹ represents an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclic group; A² represents a hydrogen atom or optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclic group; m is 0 or an integer of 1 to 4; each of A³'s represents independently a halogen atom, alkyl, alkoxy or nitro group; and A⁴ represents a halogen atom]

It is described that said compounds have excellent fungicidal activity against many kinds of Eumycetes.

Further, with regard to imidazo[1,2-a]pyrimidines which are isomers of pyrazolo[1,5-a]pyrimidines, a kind of imidazo[1,2-a]pyrimidines having herbicidal activity or fungicidal activity are disclosed. [Acta Nat. de l'Ateneo Parmense, 18 (1982) 93, J. Med. Chem. (1975) 8, 1253, etc.] However, the imidazo[1,2-a]pyrimidines having a substituent on the 6-position are not disclosed.

The present invention was made for providing novel imidazo[1,2-a]pyrimidines having excellent activity for controlling plant diseases.

DISCLOSURE OF THE INVENTION

The present inventor has earnestly studied, found that the 6-phenylimidazo[1,2-a]pyrimidines given by the formula [I] have excellent effect for controlling plant diseases and completed the present invention.

Namely, the present invention provides the imidazo[1,2-a]pyrimidine [I] (hereinafter referred to as the present compound) given by the following formula:

[wherein R¹ represents a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; phenyl group or phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring; 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group; R² represents a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; phenyl group or phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring; 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group; amino group optionally substituted by one or more selected from the group consisting of C1–C6 alkyl group, pheny group and benzyl group (said pheny group and benzyl group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C3 haloalkyl group and halogen atoms on the benzene ring); C1–C4 alkoxy group; phenoxy group; benzyloxy group; or R¹and R² together with the nitrogen atom bonded with R¹ and R² represent 3–8 membered heterocyclic group (said heterocyclic group may be substituted by C1–C4 alkylene group or C2–C4 alkenylene group to represent polycyclic heterocyclyl group, and substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group); R³ represents a halogen atom or C1–C4 alkyl group; Ar represents a phenyl group optionally substituted by one or more selected from the group consisting of halogen atoms, C1–C4 alkyl group, C1–C4 alkoxy group and C1–C3 haloalkyl group], fungicidal composition containing thereof and method for controlling plant diseases by applying it to the plants.

The present invention also provides the imidazo[1,2-a]pyrimidine [II] given by the following formula:

[wherein X represents a halogen atom, and Ar and R³ represent as defined above], the imidazo[1,2-a]pyrimidine [III] given by the following formula:

[wherein Ar represents as defined above]and

[wherein R8 represents a C1–C4 alkyl group and Ar represents as defined above], which are useful as intermediates for producing the present compounds.

In the present invention, examples of the C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms for R¹ and R² include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, sec-butyl group, isobutyl group, t-butyl group, 1-methylbutyl group, 1-ethylpropyl group, 2-methylbutyl group, 3-methylbutyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, 1,3-dimethylbutyl group, 3,3-dimethylbutyl group, 2,2-dimethylpropyl group, 2-methoxyethyl group, 3-methoxypropyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 3-butoxypropyl group, 3-isopropoxypropyl group, 2,2-dimethoxyethyl group, 2,2-diethoxyethyl group, 2-(dimethylamino)ethyl group, 2-(diethylamino)ethyl group, 2-(dipropylamino)ethyl group, 2-(dibutylamino)ethyl group, 3-(dimethylamino)propyl group, 3-(diethylamino)propyl group, 3-(dipropylamino)propyl group, 3-(dibutylamino)propyl group, 2-(methylthio)ethyl group, 2-(ethylthio)ethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, t-butoxycarbonylmethyl group, 1-(methoxycarbonyl)ethyl group, 1-(ethoxycarbonyl)ethyl group, 2-(ethoxycarbonyl)ethyl group, 1-(methoxycarbonyl)-2-methyl-1-propyl group, di(ethoxycarbonyl)methyl group, cyanomethyl group, 2-cyanoethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 3-chloropropyl group, 3-bromopropyl group, 2,5-dichloropentyl group and 1-methyl-2,2,2-trifluoroethyl group. Examples of the C3–C6 alkenyl group optionally substituted by a halogen atom or atoms for R¹ and R² include 2-propenyl group, 2-methy-2-propenyl group, 2-chloro-2-propenyl group, 3-chloro-2-propenyl group and 3,3-dichloro-2-propenyl group. Examples of the C3–C6 alkynyl group optionally substituted by a halogen atom or atoms for R¹ and R² include 2-propynyl group and 3-chloro-2-propynyl group. Examples of the C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms for R¹ and R² include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, cycloheptyl group, cyclooctyl group and 4-chlorocyclohexyl group. Examples of the phenyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring for R¹ and R² include phenyl group substituted by methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, methoxy group, ethoxy group, propoxy group, butoxy group, sec-butoxy group, methylthio group, trifluoromethyl group, trifluoromethoxy group, 1,1,2,2-tetrafluoroethoxy group, fluorine atom, chlorine atom, bromine atom, iodine atom, nitro group, cyano group, methoxycarbonyl group, ethoxycarbonyl group, propyloxycarbonyl group, butyloxycarbonyl group and so on as well as unsubstituted phenyl group. Examples of the phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring for R¹ and R² include benzyl group substituted by methyl group, trifluoromethyl group, fluorine atom, chlorine atom, bromine atom, iodine atom, methoxy group, ethoxy group, trifluoromethoxy group, nitro group, ethoxycarbonyl group, cyano group and so on as well as unsubstituted benzyl group, 1-phenylethyl group and 2-phenylethyl group. In the 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group for R¹ and R², examples of the 5 or 6 membered heterocyclic group include pyrrolidin-1-yl group, piperidin-1-yl group, piperidin-3-yl group, morpholin-4-yl group, piperadin-1-yl group, 2-thiazolin-2-yl group, isoxazol-5-yl group, isoxazol-3-yl group, isothiazol-5-yl group, thiazol-2-yl group, 1,3,4-thiadiazol-2-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyrimidin-5-yl group, pyrazin-2-yl group and 1,2,4-triazin-3-yl group. These heterocyclic group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group, and examples of said substituents include methyl group, ethyl group, fluorine atom, chlorine atom, bromine atom, methoxy group, nitro group, trifluoromethyl group, methylthio group, ethylthio group, nitro group and ethoxycarbonyl group.

In the present invention, examples of the amino group optionally substituted by one or more selected from the group consisting of C1–C6 alkyl group, phenyl group and benzyl group (said phenyl group and benzyl group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C3 haloalkyl group and halogen atoms on the benzene ring) for R² include amino group, methylamino group, dimethylamino group, t-butylamino group, phenylamino group, diphenylamino group, N-phenyl-N-methylamino group, 4-methylphenylamino group, 4-chlorophenylamino group, 3-(trifluoromethyl)phenylamino group. Examples of the C1–C4 alkoxy group for R² include methoxy group, ethoxy group and t-butoxy group.

In the present invention, examples of the 3–8 membered heterocyclic group represented by R¹ and R² together with the nitrogen atom bonded with R¹ and R² include 3–8 membered heterocyclic groups containing only one nitrogen atom as a hetero atom such as aziridin-1-yl group, azetidin-1-yl, pyrrolidin-1-yl group, 3-pyrrolin-1-yl group, pyrrol-1-yl group, piperidin-1-yl group, 1,2,3,6-tetrahydropyridin-1-yl group, hexamethyleneimin-1-yl group, heptamethyleneimin-1-yl group and so on; 3–8 membered heterocyclic groups containing two or more nitrogen atoms as hetero atoms such as 2-imidazolin-1-yl group, pyrazol-1-yl group, imidazol-1-yl group, 1,2,3-triazol-1-yl group, piperazin-1-yl group, 1,4,5,6-tetrahydropyrimidin-1-yl group, 1,2,4-triazol-1-yl group, tetrazol-1-yl group and so on; and 3–8 membered heterocyclic groups containing one nitrogen atom and one or more other hetero atoms as hetero atoms such as morpholin-4-yl group, thiazolidin-3-yl group, thiomorpholin-4-yl group and so on. Said heterocyclic groups may be substituted by C1–C4 alkylene group (methylene group, ethylene group, trimethylene group, tetramethylene group) or C2–C4 alkenylene group (vinylene group, propenylene group, 2-butenylene group, 1,3-butadienylene group) and examples of the polycyclic hetrocyclyl group formed of the 3–8 membered heterocyclic group substituted by said C1–C4 alkylene group or C2–C4 alkenylene group include 2-azabicyclo[2.2.1]heptan-2-yl group, 7-azabicyclo[2.2.1]heptan-7-yl group, 2-azabicyclo[2.2.2]octan-2-yl group, 3-azabicyclo[3.2.1]octan-3-yl group, 2-azabicyclo[3.2.1]octan-2-yl group, 6-azabicyclo[3.2.1]octan-6-yl group, 8-azabicyclo[3.2.1]octan-8-yl group, 3-azabicyclo[3.2.2]nonan-3-yl group, 6-azabicyclo[3.2.2]nonan-6-yl group, 2-azabicyclo[3.3.0]octan-2-yl group, 3-azabicyclo[3.3.0]octan-3-yl group, 2-azabicyclo[4.3.0]nonan-2-yl group, 3-azabicyclo[4.3.0]nonan-3-yl group, 7-azabicyclo[4.3.0]nonan-7-yl group, 8-azabicyclo[4.3.0]nonan-8-yl group, 2-azabicyclo[4.4.0]decan-2-yl group, 3-azabicyclo[4.4.0]decan-3-yl group, indolin-1-yl group, 1,2,3,4-tetrahydroquinolin-1-yl group, 1,2,3,4-tetrahydroisoquinolin-2-yl group, indol-1-yl group, indazol-1-yl group and benzimidazol-1-yl group. These heterocyclic group may be further substituted by one or more selected from the group consisting of C1–C4 alkyl group (e.g. methyl group, ethyl group, propyl group, isopropyl group), C1–C4 alkoxy group (e.g. methoxy group), C1–C4 alkylthio group (e.g. methylthio group), C1–C3 haloalkyl group (e.g. trifluoromethyl group), C1–C4 acyl group (e.g. formyl group, acetyl group), halogen atoms (e.g. chlorine atom, bromine atom, iodine atom), hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group (e.g. methoxycarbonyl group, ethoxycarbonyl group, propyloxycarbonyl group, t-butoxycarbonyl group).

Preferable embodiments for R¹R²N in the present compounds are ones wherein R¹ and R² independently represent a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atom; or wherein R¹ and R² together with the nitrogen atom bonded with R¹ and R² represent 3–8 membered heterocyclic group optionally substituted by C1–C4 alkylene group or C2–C4 alkenylene group, or optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, trifluoromethyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group. More preferable embodiments are ones wherein R¹ and R² independently represent C1–C6 alkyl group optionally substituted by a halogen atom or atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; wherein R¹ and R² together with the nitrogen atom bonded with R¹ and R² represent pyrrolidin-1-yl group, 3-pyrrolin-1-yl group, piperidin-1-yl group, 1,2,3,6-tetrahydropyridin-1-yl group, hexamethyleneimin-1-yl group, piperazin-1-yl group, morpholin-4-yl group and thiomorpholin-4-yl group optionally substituted by a C1–C4 alkyl group or groups.

In the present invention, examples of the halogen atom for R³ include fluorine atom, chlorine atom, bromine atom and iodine atom. Examples of the C1–C4 alkyl group for R³ include methyl group, ethyl group, propyl group, isopropyl group and t-butyl group.

Preferable embodiments for R³ in the present compounds are a chlorine atom or methyl group.

In the present invention, examples of the phenyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group and C1–C3 haloalkyl group for Ar include phenyl groups substituted by fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, t-butyloxy group, trifluoromethyl group and so on as well as unsabstituted phenyl group

Preferable embodiments for Ar in the present compounds are phenyl groups substituted by a halogen atom or atoms at one or more of 2-, 4- and 6-positions, and more preferable embodiments are phenyl groups substituted by fluorine atoms or chlorine atoms at two or more of 2-, 4- and 6-positions and unsubstituted at 3- and 5-positions. Typical examples are 2-chlorophenyl group, 2-fluorophenyl group, 2,6-dichlorophenyl group, 2,6-difluorophenyl group, 2,4-dichlorophenyl group, 2,4-difluorophenyl group, 2-chloro-6-fluorophenyl group, 2,4,6-trifluorophenyl group, 4-chloro-2,6-difluorophenyl group, 2-chloro-4,6-difluorophenyl group, 2,6-dichloro-4-fluorophenyl group, 2,4-dichloro-6-fluorophenyl group and 2,4,6-trichlorophenyl group.

The present compounds may have asymmetric carbon atom(s) and double bond(s), and the scope of the present invention include mixtures at any ratio of the optical isomers ((+)-form, (−)-form) and geometrical isomers and each of the pure isomers. Further, the salts of the present compounds are also within the scope of the present invention.

Examples of the present compounds having excellent effect for controlling plant diseases include 5-(piperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(4-methylpiperidin-1-yl) -6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(2-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(morpholin-4-yl) -6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(thiomorpholin-4-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(hexamethyleneimin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(2,5-dimethylpyrrolidin-1-yl)-6-(2,4, 6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-dipropylamino-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-diallylamino-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(piperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(2-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(morpholin-4-yl)-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(thiomorpholin-4-yl)-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(hexamethyleneimin-1-yl)-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(2,5-dimethylpyrrolidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-dipropylamino-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-diallylamino-6-(2,4,6-trifluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(piperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo [1,2-a]pyrimidine, 5-(2-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(morpholin-4-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(thiomorpholin-4-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(hexamethyleneimin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(2,5-dimethylpyrrolidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-dipropylamino-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-diallylamino-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(piperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo [1,2-a]pyrimidine, 5-(2-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(morpholin-4-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(thiomorpholin-4-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(hexamethyleneimin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(2,5-dimethylpyrrolidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-dipropylamino-6-(2-chloro-6-fluorophenyl)-7-methylimidazo [1,2-a]pyrimidine, 5-diallyamino-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(piperidin-1-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(4-methylpiperidin-1-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(2-methylpiperidin-1-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(morpholin-4-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(thiomorpholin-4-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(hexamethyleneimin-1-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(2,5-dimethylpyrrolidin-1-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-dipropylamino-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-diallylamino-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine, 5-(piperidin-1-yl)-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(4-methylpiperidin-1-yl)-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(2-methylpiperidin-1-yl)-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(morpholin-4-yl)-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(thiomorpholin-4-yl)-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(hexamethyleneimin-1-yl)-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-(2,5-dimethylpyrrolidin-1-yl)-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 5-dipropylamino-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine and 5-diallylamino-6-(2,6-difluorophenyl)-7-methylimidazo[1,2-a]pyrimidine.

The present compound can be produced by making the imidazo[1,2-a]pyrimidine [II] react with an amine [V] of the following formula:

[wherein R¹ and R² have the same meanings as defined above]. The theoretical amount of the amine [V] is one mole based on one mole of the imidazo[1,2-a]pyrimidine [II], but the used amount can be varied according to the reaction condition.

The reaction can be performed without solvent or in an inert solvent. Examples of the solvent used for the reaction include ethers such as dioxane, diethyl ether, tetrahydrofuran, methyl t-butyl ether and so on; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and so on; hydrocarbons such as toluene, benzene, xylene and so on; aprotic polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide and so on; alcohols such as methanol, ethanol, isopropyl alcohol and so on.

The reaction can be performed in the presence of a base. One mole or more of the base is usually used based on one mole of the imidazo[1,2-a]pyrimidine [II]. Examples of the base used for the reaction include organic bases such as pyridine, 2,6-lutidine, triethylamine, N,N-diisopropylethylamine, diazabicycloundecene (DBU), diazabicyclononene (DBN) and so on; and inorganic bases such as potassium carbonate, sodium hydride and so on. It may be possible to give the same effect as one by using said base when an excessive amount of the amine [V] is used.

The reaction temperature is usually in the range of 0° C. to 200° C. It is selected dependently on the reaction rate from the above range. The reaction can be performed at a higher temperature than the boiling point of the amine [V] or the solvent by using an autoclave as a reaction container.

The termination of the reaction can be identified by analyzing the residual amount of the imidazo[1,2-a]pyrimidine [II] with a method of thin-layer chromatography, high pressure liquid chromatography or the like.

After the reaction, usual work-up procedures, for example pouring the reaction liquid into water, extracting with organic solvent and concentration, give the present compound. Further, the present compound can be purified by recrystallization, chromatography and so on.

The amine [V] is a known compound, or can be prepared according to known methods from known compounds.

The imidazo[1,2-a]pyrimidine [II] can be prepared by the following scheme.

(Production Route a)

[wherein R⁹ represents a methyl group or ethyl group; HA represents a mineral acid (e.g. hydrochloric acid, sulfuric acid); Ar and X have the same meanings described above] (Production Route b)

[wherein R⁸ represents a C1–C4 alkyl group; R⁹, HA, Ar and X have the same meanings described above]

The diester compound [VI] that is a starting material of Production route (a) is a known compound (described in JP hei2-202876A, Chemistry Letters, 1981, p. 367 and so on) or can be prepared according to a known method. The β-ketoester [VII] that is a starting material of Production route (b) is known in Organic Synthesis Collective Volume 2, pp. 487–489 and pp. 284–286, JP sho60-255788A and so on, or can be prepared according to a known method.

The 2-aminoimidazole mineral acid salt [VIII] that is a common starting material to Production routes (a) and (b) is known in J. Chem. Soc., 1956, 307, J. Org. Chem., 1964, 3118 and so on.

Step (a)-1

The imidazo[1,2-a]pyrimidine [III] can be prepared by making the diester [VI] react with the 2-aminoimidazole mineral acid salt [VIII].

The theoretical amount is one mole of the 2-aminoimidazole mineral acid salt [VIII] based on one mole of the diester [VI], but the amount can be varied according to the reaction condition. The reaction is carried out in the presence of a base without solvent or in a inert solvent at 50° C. to 200° C. Examples of the base include organic bases such as tri-n-butylamine, diazabicycloundecene (DBU), diazabicyclononene (DBN) and so on. The amount of the base used for the reaction is one mole or more based on one mole of the total of the diester [VI] and the 2-aminoimidazole mineral acid salt [VIII]. Examples of the solvent used for the reaction include hydrocarbons such as mesitylene and so on, and aprotic polar solvents such as N,N-dimethylformamide (DMF) and so on.

The termination of the reaction can be identified by analysing the residual amount of the diester [VI] by a method of thin layer chromatography, high pressure liquid chromatography or the like.

After the reaction, for example, a hydrophobic organic solvent and water are added to the reaction mixture, the separated water layer is optionally concentrated, treated with an acid such as hydrochloric acid and the precipitate is filtered to give the imidazo[1,2-a]pyrimidine [III]. Alternatively, the reaction mixture is optionally concentrated and then filtered to give a salt of the imidazo[1,2-a]pyrimidine [III]. The obtained imidazo[1,2-a]pyrimidine [III] can be further purified by recrystallization or the like.

Step (a)-2

The imidazo[1,2-a]pyrimidine [II-1], which is an imidazo[1,2-a]pyrimidine [II] wherein R³ is a halogen atom, can be prepared by making the imidazo[1,2-a]pyrimidine [III] or its salt react with a halogenating agent.

Examples of the halogenating agent used for the reaction include phosphorus oxychloride and phosphorus oxybromide.

The reaction is carried out without solvent or in an inert solvent (e.g. hydrocarbons such as toluene, nitrites such as acetonitrile, halogenated hydrocarbons such as ethylene dichloride) at 80° C. to 150° C. The reaction may be accelerated by the presence of a base, and examples of the base include organic bases such as N,N-diethylaniline, N,N-dimethylaniline, triethylamine, N,N-diisopropylethylamine, pyridine, 5-ethyl-2-picoline, DBU and DBN.

The termination of the reaction can be identified by analysing the residual amount of the imidazo[1,2-a]pyrimidine [III] by a method of thin layer chromatography, high pressure liquid chromatography or the like.

After the reaction, usual work-up procedures such as removing an excess of the halogenating agent, pouring the residue into water, extracting it with an organic solvent and concentrating it to give the imidazo[1,2-a]pyrimidine [II-1]. The obtained imidazo[1,2-a]pyrimidine [II-1] can be further purified by recrystallization, chromatography or the like.

Step (b)-1

The imidazo[1,2-a]pyrimidine [IV] can be prepared by making the β-ketoester [VII] react with the 2-aminoimidazole mineral acid salt [VIII].

The theoretical amount is one mole of the 2-aminoimidazole mineral acid salt [VIII] based on one mole of the 6-ketoester [VII], but the amount can be varied according to the reaction condition. The reaction is carried out in the presence of a base, without solvent or in an inert solvent at the temperature of 50° C. to 200° C. Examples of the base include organic bases such as tri-n-butylamine, diazabicycloundecene (DBU), diazabicyclononene (DBN) and so on. The amount of the base used for the reaction is one mole or more base on one mole of the total of the 8-ketoester [VII] and the 2-aminoimidazole mineral acid salt [VIII]. Examples of the solvent used for the reaction include hydrocarbons such as mesitylene and so on, and aprotic polar solvents such as N,N-dimethylformamide and so on.

The termination of the reaction can be identified by analysing the residual amount of the β-ketoester [VII] by a method of thin layer chromatography, high pressure liquid chromatography or the like.

After the reaction, for example, a hydrophobic organic solvent and water are added to the reaction mixture, the separated water layer is optionally concentrated and treated with an acid such as hydrochloric acid to give a precipitate of the imidazo[1,2-a]pyrimidine [IV]. Alternatively, the reaction mixture is optionally concentrated and then filtered to give a salt of the imidazo[1,2-a]pyrimidine [IV] The obtained imidazo[1,2-a]pyrimidine [IV] can be further purified by recrystallization or the like.

Step (b)-2

The imidazo[1,2-a]pyrimidine [II-2], which is an imidazo[1,2-a]pyrimidine [II] wherein R³ is a C1–C4 alkyl group, can be prepared by making the imidazo[1,2-a]pyrimidine [IV] or its salt react with a halogenating agent.

Examples of the halogenating agent used for the reaction include phosphorus oxychloride and phosphorus oxybromide.

The reaction is carried out without solvent or in a inert solvent (e.g. hydrocarbons such as toluene, nitrites such as acetonitrile, halogenated hydrocarbons such as ethylene dichloride) at 80° C. to 150° C. The reaction may be accelerated by the presence of a base, and examples of the base include organic bases such as N,N-diethylaniline, N,N-dimethylaniline, triethylamine, N,N-diisopropylethylamine, pyridine, 5-ethyl-2-picoline, DBU and DBN.

The termination of the reaction can be identified by analysing the residual amount of the imidazo[1,2-a]pyrimidine [IV] by a method of thin layer chromatography, high pressure liquid chromatography or the like.

After the reaction, usual work-up procedures such as removing an excess of halogenating agent, pouring the residue into water, extracting it with an organic solvent and concentrating it to give the imidazo[1,2-a]pyrimidine [II-2]. The obtained imidazo[1,2-a]pyrimidine [II-2] can be further purified by recrystallization, chromatography or the like.

When the present compound is used as an active ingredient of a fungicide, it may be used without other ingredients; however, it is usually formulated by mixing a solid carrier, liquid carrier, surfactant, or the other formulation auxiliary to emulsifiable concentrates, wettable powders, water dispersible granules, emulsion formulations, flowables, dusts, granules and so on. These formulations usually contain 0.1 to 90% by weight of the present compound as an active ingredient.

Examples of the solid carrier include minerals such as kaolin clay, attapulgite clay, bentonite, montmorillonite, terra alba, pyrophillite, talc, diatomaceous earth, calcite and so on; natural organisms such as corncob powder, walnut shell powder and so on; synthetic organisms such as urea and so on; and salts such as calcium carbonate, ammonium sulfate and so on. Examples of the liquid carrier include aromatic hydrocarbons such as xylene, alkylbenzene, methylnaphthalene and so on; alcohols such as isopropanol, ethylene glycol, propylene glycol, cellosolve and so on; ketones such as acetone, cyclohexanone, isophorone and so on; vegetable oils such as soybean oil, cotton seed oil and so on; petroleum aliphatic hydrocarbons; esters; dimethyl sulfoxide; acetonitrile; and water.

Examples of the surfactant include anionic surfactants such as alkylsulfate ester salts, alkylarylsulfonic acid salts, dialkylsulfosuccinic acid salts, polyoxyethylene alkyl aryl ether phosphate ester salts, ligninsulfonic acid salts, naphthalenesulfonate formaldehyde condensate and so on; and nonionic surfactants such as polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl polyoxypropylene block copolymer, sorbitan fatty acid ester and so on.

Examples of the formulation auxiliary include water soluble polymers such as polyvinyl alcohol, polyvinylpyrrolidone and so on; gum arabic; alginic acid and its salts; polysaccharides such as CMC (carboxymethylcellulose) and xanthan gum; inorganic materials such as aluminum magnesium silicate and alumina sol; preservatives; coloring agents; and stabilizers such as PAP (isopropyl acid phosphate) and BHT.

When the present compound is used for controlling plant diseases, it typically applied by the methods of foliar treatment, soil treatment and so on. The application dosage can be varied according to the type of the protected plant, the type of the disease to be controlled, degree of affection by the disease, formulation type, application method, time of application, weather conditions and so on, and it is usually 1 to 5000 g, preferably 5 to 1000 g per one hectare. In case that emulsifiable concentrate, wettable powder, suspensible concentrate or the like is diluted with water and applied, the application concentration of the active ingredientis 0.0001 to 3% by weight, preferably 0.0005 to 1% by weight. Dusts, granules and the like are applied without dilution as they are.

Further, the present compound can be applied by the other usual methods such as seed disinfection and so on. In the case of seed treatment, seeds are usually soaked in a dilution of the present compound made 1 to 1000 ppm of the concentration, or the dilution is sprayed to or painted the seeds, alternatively, the seeds are treated with the dusts containing the present compound at 0.1 to 10% by weight.

The present compound can be used as an effective ingredient of fungicide for controlling plant diseases in upland field, paddy field, orchard, tea field, pasture, lawn and the like. It may occasionally be expected to increase the fungicidal effect by mixing with the other fungicide. Examples of the fungicide include azole fungicidal compounds such as propiconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxyconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, flutriafol and so on; cyclic amine fungicidal compounds such as fenpropimorph, tridemorph, fenpropidin and so on; benzimidazole fungicidal compounds such as carbendazim, benomyl, thiabendazole, thiophanate-methyl and so on; procymidone; cyprodinil; pyrimethanil; diethofencarb; thiuram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil; captan; mepanipyrim; fenpiclonil; fludioxonil; dichlorfluanid; folpet; kresoxim-methyl; azoxystrobin; trifloxystrobin; picoxystrobin; pyraclostrobin; N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy)methyl]phenylacetamide; spiroxamine; quinixyfen; fenhexamide; famoxadone; fenamidone; iprovalicard; benthiavalicarb; pencycuron; flutolanil; furametpyr; phthalide; carpropamid; diclocymet; probenazole; blasin; cyazofamid; nicobifen and metrafenone.

The present compound may be used together with the other agricultural or horticultural insecticide, acaricide, nematicide, herbicide, plant growth regulator and fertilizer. It may be blended in advance of the application.

Examples of the insecticide, acaricide and nematicide include organophosphorus compounds such as fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate], fenthion [O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl)phosphorothioate], diazinon [O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate], chlorpyrifos [O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate], acephate [O,S-dimethyl acetylphosphoramidethioate], methidathion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethyl phosphorodithioate], disulfoton [O,O-diethyl S-2-ethylthioethyl phosphorothioate], DDVP [2,2-dichlorovinyl dimethyl phosphate], sulprofos, [O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate], cyanophos [O-4-cyanophenyl O,O-dimethyl phosphorothioate], dioxabenzofos [2-methoxy-4H-1,3,2-benzodioxaphosphorin-2-sulfide], dimethoate [O,O-dimethyl S-(N-methylcarbamoylmethy)dithiophosphate], phenthoate [ethyl 2-dimethoxyphosphinothioylthio(phenyl)acetate], malathion [diethyl(dimethoxyphosphinothioylthio)succinate], trichlorfon [dimethyl2,2,2-trichloro-1-hydroxyethylphosphonate], azinphos-methyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O,O-dimethyl phosphorodithioate], monocrotophos [dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinyl phosphate], ethion [O,O,O′,O′-tetraethyl S,S′-methylenebis(phosphorodithioate)], fosthiazate [N-(O-methyl-S-sec-butyl) phosphorylthiazolidin-2-one] and so on; carbamate compound such as BPMC [2-sec-butylphenyl methylcarbamate], benfuracarb [ethyl N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio)-N-isopropyl-β-alaninate, propoxur [2-isopropylphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-2,2-dimethyl-7-benzo[b]furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl N-methylcarbamate], methomyl [S-methyl-N-[(methylcarbamoyl)oxy]thioacetoimidate], ethiofencarb [2-(ethylthiomethyl)phenyl methylcarbamate], aldicarb [2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime], oxamyl [N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide], fenothiocarb [S-4-phenoxybutyl-N,N-dimethylthiocarbamate] and so on; pyrethroid compounds such as etofenprox [2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether], fenvalerate [(RS)-α-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate], esfenvalerate [(S)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate], fenpropathrin [(RS)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], cypermethrin [(RS)-α-cyano-3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1RS, 3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], cyhalothrin [(RS)-α-cyano-3-phenoxybenzyl (Z)-(1RS,3RS)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S)-α-cyano-m-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate], cycloprothrin [(RS)-α-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], fluvalinate [α-cyano-3-phenoxybenzyl N-(2-chloro-α,α,α-trifluoro-p-tolyl)-D-valinate], bifenthrin [2-methylbiphenyl-3-ylmethyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], acrinathrin [cyano(3-phenoxyphenyl)methyl (1R-{1α(S*),3α(Z)})-2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoro-1-(trifluoromethyl)ethoxy-1-propenyl)cyclopropanecarboxylate], 2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl 3-phenoxybenzyl ether, tralomethrin [(S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(1,2,2,2-tetrabromoethyl)-2,2-dimethylcyclopropanecarboxylate], silafluofen [4-ethoxyphenyl(3-(4-fluoro-3-phenoxyphenyl)propyl) dimethylsilane] and so on; thiadiazine derivatives such as buprofezin (2-t-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one) and so on; nitroimidazolidine derivatives; nereistoxin derivatives such as cartap (S,S′-(2-dimethylaminotrimethylene) bis(thiocarbamate)), thiocyclam [N,N-dimethyl-1,2,3-trithian-5-ylamine], bensultap [S,S′-2-dimethylaminotrimethylene di(benzenethiosulfonate)] and so on; N-cyanoamidine derivatives such as N-cyano-N′-methyl-N′-(6-chloro-3-pyridylmethyl)acetamidine and so on; chlorinated hydrocarbon compounds such as endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine oxide], γ-BHC (1,2,3,4,5,6-hexachlorocyclohexane), 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol and so on; benzoylphenylurea compounds such as chlorfluazuron [1-(3,5-dichloro-4-(3-chloro -5-trifluoromethylpyridin-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl)urea], teflubenzuron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl) urea], flufenoxuron [1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)urea] and so on; formamidine derivatives such as amitraz [N,N′[(methylimino) dimethylidine]di-2,4-xylidine], chlordimeform [N′-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide] and so on; thiourea derivatives such as diafenthiuron [N-(2,6-diisopropyl-4-phenoxyphenyl)-N′-t-butylcarbodiimide] and so on; phenylpyrazole compounds; tebufenozide [N-t-butyl-N′-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide]; 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile; bromopropylate [isopropyl 4,4′-dibromobenzilate]; tetradifon [4-chlorophenyl2,4,5-trichlorophenylsulfone]; chinomethionat [S,S-6-methylquinoxalin-2,3-diyl dithiocarbonate]; propargite [2-(4-t-butylphenoxy)cyclohexyl prop-2-yl sulfite]; fenbutatin oxide [bis[tris(2-methyl-2-phenylpropyl)tin]oxide]; hexythiazox [(4RS,5RS)-5-(4-chlorophenyl)-N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide];clofentezine [3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine]; pyridathioben [2-t-butyl-5-(4-t-butylbenzylthio)-4-chloropyridazin-3(2H)-one]; fenpyroximate [t-butyl (E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl) methyleneaminooxymethyl]benzoate]; tebufenpyrad [N-4-(t-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide]; polynactin complex [tetranactin, dinactin, trinactin]; milbemectin; avermectin; ivermectin; azadirachtin [AZAD]; pyrimidifen [5-chloro-N-[2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxy}ethyl]-6-ethylpyrimidin-4-amine]; and pymetrozine [2,3,4,5-tetrahydro-3-oxo-4-[(pyridine-3-yl)methyleneamino]-6-methyl-1,2,4-triazine].

Examples of the plant diseases to be controlled by the present compound include Pyricularia oryzae and Cochliobolus miyabeanus and Rhizoctonia solani of rice; Erysiphe graminis, Gibberella zeae, Puccinia striiformis, P. graminis, P. recondita, P. hordei, Typhula sp., Micronectriella nivalis, Ustilago tritici, U. nuda, Tilletia caries, Pseudocercosporella herpotrichoides, Rhynchosporium secalis, Septoria tritici and Leptosphaeria nodorum, of wheat and barley; Diaporthe citri, Elsinoe fawcetti, Penicillium digitatum and P. italicum of citrus; Sclerotinia mali, Valsa mali, Podosphaera leucotricha, Alternaria mali and Venturia inaequalis of apple; Venturia nashicola, V. pirina, Alternaria kikuchiana and Gymnosporangium haraeanum of pear; Sclerotinia cinerea, Cladosporium carpophilum and Phomopsis sp. of peach; Elsinoe ampelina, Glomerella cingulata, Uncinula necator, Phakopsora ampelopsidis, Guignardia bidwellii and Plasmopara viticola, of grape; Gloeosporium kaki, Cercospora kaki and Mycosphaerella nawae of Japanese persimmon; Colletotrichum lagenarium, Sphaerothecafuliginea, Mycosphaerella melonis, Fusarium oxysporum, Pseudoperonospora cubensis Phytophthora sp. and Pythium sp. of gourd; Alternaria solani; Cladosporium fulvum and Phytophthora infestans of tomato; Phomopsis vexans and Erysiphe cichoracearum, of eggplant; Alternaria japonica and Cercosporella brassicae of Cruciferae vegetables; Puccinia allii of leek; Cercospora kikuchii, Elsinoe glycines and Diaporthe phaseolorum var. sojae of soybean; Colletotrichum lindemthianum of kidney bean; Cercospora personata and Cercospora arachidicola of peanut; Erysiphe pisi of pea; Alternaria solani and Phytophthora infestans of potato; Sphaerotheca humuli of strawberry; Exobasidium reticulatum and Elsinoe leucospila of tea; Alternaria longipes, Erysiphe cichoracearum, Colletotrichum tabacum, Peronospora tabacina and Phytophthora nicotianae of tobacco; Cercospora beticola of sugar beet; Diplocarpon rosae and Sphaerotheca pannosa of rose; Septoria chrysanthemi-indici and Puccinia horiana of chrysanthemum; and Botrytis cinerea and Sclerotinia sclerotiorum of various crops.

Hereinafter, the present invention is explained by production examples, formulation examples and test examples in more detail. The present invention is not restricted by the examples.

At first, the production examples of the present compounds are given below.

PRODUCTION EXAMPLE 1 5-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine (Compound 55) (a) Preparation of diethyl (2,4,6-trifluorophenyl)malonate

Into a mixture of 4.8 g of sodium hydride (60% in oil) and 100 ml of 1,4-dioxane, 19.2 g of diethyl malonate were added dropwise at room temperature, and then 17.2 g of cuprous bromide and 21.1 g of 1-bromo-2,4,6-trifluorobenzene were subsequently added thereto at 40° C. and refluxed for 26 hours under heating. To the reaction mixture, conc. hydrochloric acid was added under ice-cooling, and then tert-butyl methyl ether and water were added. The organic layer was separated, washed with aqueous sodium hydroxide solution, dil. hydrochloric acid and water subsequently, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 12.6 g of diethyl (2,4,6-trifluorophenyl)malonate.

¹H-NMR(CDCl₃,TMS)δ(ppm): 1.28 (3H, t, J=7.1 Hz), 4.26 (2H, q, J=7.1 Hz), 4.89 (1H, s), 6.71 (2H, t, J=8.2 Hz)

(b) Preparation of 5,7-dihydroxy-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine

A mixture of 2.90 g of diethyl (2,4,6-trifluorophenyl)malonate, 2.39 g of 2-aminoimidazole hydrochloride, 4.57 g of DBU and 10 ml of N,N-dimethylformamide was heated at 100° C. for 6 hours. After allowing the reaction mixture to cool to room temperature, chloroform and water were added thereto. The separated water layer was concentrated, the residue was diluted with water and conc. hydrochloric acid was added thereto under ice-cooling. The precipitation was filtered and dried to give 2.2 g of 5,7-dihydroxy-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine.

(c) Preparation of 5,7-dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine

A mixture of 2.11 g of 5,7-dihydroxy-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine and 5 ml of phosphorus oxychloride was refluxed under heating for 24 hours. After the reaction mixture was concentrated, dichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue. The separated organic layer was washed with aqueous sodium bicarbonate solution and saturated brine, subsequently, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 1.39 g of 5,7-dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine.

(d) Preparation of 5-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine

Under ice-cooling, 0.64 g of 5,7-dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine and 0.79 g of 4-methylpiperidine were mixed. The mixture was allowed to stand at room temperature for one hour, and chloroform and aqueous saturated ammonium chloride solution were added to the reaction mixture. The separated organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was washed with t-butyl methyl ether to give 0.62 g of 5-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine

PRODUCTION EXAMPLE 2 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine (Compound 182) (a) Preparation of diethyl (2-chloro-6-fluorophenyl)malonate

Into a mixture of 7.2 g of sodium hydride (60% in oil), 17.0 g of diethyl carbonate and 150 ml of tetrahydrofuran, 26.0 g of ethyl 2-chloro-6-fluorophenylacetate were added dropwise under heating, and then refluxed under heating for 8 hours. The reaction mixture was cooled, poured into iced dil. hydrochloric acid and extracted with t-butyl methyl ether. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 30.4 g of diethyl (2-chloro-6-fluorophenyl)malonate.

¹H-NMR(CDCl₃,TMS)δ(ppm): 1.28 (3H, t, J=7.1 Hz), 4.26 (2H, q, J=7.1 Hz), 5.16 (1H, s), 7.0–7.1 (1H, m), 7.2–7.4 (2H, m)

(b) Preparation of 5,7-dihydroxy-6-(2-chloro-6-fluorophenyl)imidazo[1,2-a]pyrimidine DBN salt

A mixture of 2.89 g of diethyl (2-chloro-6-fluorophenyl)malonate, 1.20 g of aminoimidazole hydrochloride, 2.48 g of 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) and 10 ml of N,N-dimethylformamide (DMF) was heated at 100° C. for 4 hours. The reaction mixture was allowed to cool, filtered the precipitate and dried to give 1.80 g of 5,7-dihydroxy-6-(2-chloro-6-fluorophenyl)imidazo[1,2-a]pyrimidine DBN salt.

(c) Preparation of 5,7-dichloro-6-(2-chloro-6-fluorophenyl)imidazo[1,2-a]pyrimidine

A mixture of 1.62 g of 5,7-dihydroxy-6-(2-chloro-6-fluorophenyl)imidazo[1,2-a]pyrimidine DBN salt and 5 ml of phosphorus oxychloride was refluxed under heating for 10 hours. The reaction mixture was concentrated, and dichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue. The separated organic layer was washed with aqueous saturated sodium bicarbonate and water subsequently, dried over sodium sulfate and concentrated. The residue was subjected to silica gel chromatography to give 1.00 g of 5,7-dichloro-6-(2-chloro-6-fluorophenyl)imidazo[1,2-a]pyrimidine.

(d) Preparation of 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine

Under ice-cooling, 0.63 g of 5,7-dichloro-6-(2-chloro-6-fluorophenyl)imidazo[1,2-a]pyrimidine and 0.79 g of 4-methylpiperidine were mixed. The reaction mixture was allowed to stand at room temperature for 10 minutes, and chloroform and water were added thereto. The separated organic layer was with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel chromatography to give 0.73 g of 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine.

PRODUCTION EXAMPLE 3 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine (Compound 428) (a) Preparation of ethyl 2-(2-chloro-6-fluorophenyl)acetoacetate

Into a mixture of 9.6 g of sodium hydride (60% in oil) and 200 ml of tetrahydrofuran, 21.7 g of ethyl 2-chloro-6-fluorophenylacetate were added dropwise under reflux. Then, a solution of 12.3 g of acetic anhydride in 40 ml tetrahydrofuran was added thereto and refluxed under heating for 10 hours. The reaction mixture was cooled, poured into iced dil. hydrochloric acid and extracted with t-butyl methyl ether. The organic layer was washed with dil. hydrochloric acid, aqueous saturated sodium bicarbonate solution, dil. hydrochloric acid and water, subsequently, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 9.27 g of ethyl (2-chloro-6-fluorophenyl)acetoacetate.

¹H-NMR(CDCl₃,TMS)δ(ppm): 1.17 (3H, t, J=7.1 Hz), 1.82 (3H, s), 4.1–4.3 (2H, m), 6.9–7.1 (1H, m), 7.2–7.3 (2H, m), 13.2 (1H, s)

(b) Preparation of 5-hydroxy-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

A mixture of 1.29 g of ethyl (2-chloro-6-fluorophenyl)acetoacetate, 0.60 g of aminoimidazole hydrochloride, 1.24 g of 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) and 5 ml of N,N-dimethylformamide was heated at 100° C. for 14 hours. The reaction mixture was allowed to cool, and chloroform and water were added thereto. To the separated water layer, conc. hydrochloric acid was added and the precipitate was filtered, which was followed to subject to silica gel chromatography to give 0.16 g of 5-hydroxy-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine.

(c) Preparation of 5-chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

A mixture of 0.16 g of 5-hydroxy-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 0.20 g of N,N-diethylaniline and 2 ml of phosphorus oxychloride was refluxed under heating for 26 hours. The reaction mixture was concentrated, and dichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue. The separated organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel chromatography to give 45mg of 5-chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine.

(d) Preparation of 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

At room temperature, 45 mg (0.16 mmol) of 5-chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine and 63 mg (0.64 mmol) of 4-methylpiperidine were mixed. After one hour, chloroform and aqueous saturated ammonium chloride solution were added to the reaction mixture. The separated organic layer was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was subjected to silica gel chromatography to give 35 mg (0.10 mmol, 61%) of 5-(4-methylpiperidin-1-yl)-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine.

PRODUCTION EXAMPLE 4 5-amino-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine (Compound 1)

A mixture of 0.48 g (1.5 mmol) of 5,7-dichloro-6-(2,4,6-trifluorophenyl)-imidazo[1,2-a]pyrimidine, 5 ml of aqueous ammonia and 10 ml of ethanol was refluxed under heating for 8 hours. The reaction mixture was concentrated.

Water was added to the residue, and the precipitate was obtained by filtration and dried to give 0.30 g (1.0 mmol, 68%) of 5-amino-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine.

PRODUCTION EXAMPLE 5 5-(di-n-propylamino)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine (Compound 8)

A mixture of 0.095 g of 5,7-dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine and 0.12 g of di-n-propylamine was heated at 80° C. for one hour. The reaction mixture was allowed to cool, and chloroform and water were added thereto. The separated organic layer was dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 0.095 g of 5-(di-n-propylamino)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine.

PRODUCTION EXAMPLE 6 5-(2-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine (Compound 53)

A mixture of 0.63 g of 5,7-dichloro-6-(2,4,6-trifluorophenyl)-imidazo[1,2-a]pyrimidine, 0.79 g of 2-methylpiperidine and 2 ml of chloroform was heated at 80° C. for one hour. The reaction mixture was allowed to cool and subjected to silica gel column chromatography to give 0.30 g of 5-(2-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine.

PRODUCTION EXAMPLE 7 5-(hexamethyleneimin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine (Compound 72)

At room temperature, 0.32 g of 5,7-dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine and 0.40 g of hexamethyleneimine were mixed. After 18 hours, water was added to the reaction mixture and the precipitate was obtained by filtration. The filtrate was subjected to silica gel column chromatography to give 0.35 g of 5-(hexamethyleneimin-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine.

PRODUCTION EXAMPLE 8 5-(3,5-dimethylpyrazol-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine (Compound 89)

Into a mixture of 0.040 g of sodium hydride (60% in oil) and 2 ml of tetrahydrofuran, a solution of 0.096 g of 3,5-dimethylpyrazole in 3 ml of tetrahydrofuran was added dropwise. The mixture was added to a solution of 0.32 g of 5,7-dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine in 5 ml of tetrahydrofuran under ice-cooling. To the reaction mixture, chloroform and aqueous citric acid solution were added. The separated organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 0.18 g of 5-(3,5-dimethylpyrazol-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine.

PRODUCTION EXAMPLE 9 5-(hexamethyleneimine-1-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine (Compound 233) (a) Preparation of diethyl (2,6-difluorophenyl)malonate

Into a mixture of 8.00 g of sodium hydride (60% in oil) and 100 ml of 1,4-dioxane, 32.0 g of ethyl malonate were added dropwise at 60° C. , further 14.6 g of cuprous bromide and 19.3 g of 1-bromo-2,6-difluorobenzene were added subsequently, and then refluxed for 16 hours under heating. To the reaction mixture, conc. hydrochloric acid was added under ice-cooling, and then tert-butyl methyl ether and water were added. The separated organic layer was washed with dil. hydrochloric acid and water subsequently, dried over sodium sulfate and concentrated. The residue was distilled under reduced pressure to give 16.5 g of diethyl (2,6-difluorophenyl)malonate. b.p. 107–109° C. (0.14 mmHg)

(b) Preparation of 5,7-dihydroxy-6-(2,6-difluorophenyl)imidazo[1,2-a]pyrimidine

A mixture of 13.6 g of diethyl (2,6-difluorophenyl)malonate, 7.93 g of 2-aminoimidazole sulfate, 9.13 g of DBU and 30 ml of N,N-dimethylformamide was heated at 100° C. for 7 hours. To the reaction mixture, water was added and allowed to cool to room temperature, and t-butyl methyl ether was added thereto. To the separated water layer, conc. hydrochloric acid was added and the precipitate was obtained by filtration and dried to give 7.84 g of 5,7-dihydroxy-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine.

(c) Preparation of 5,7-dichloro-6-(2,6-difluorophenyl)imidazo[1,2-a]pyrimidine

A mixture of 7.63 g of 5,7-dihydroxy-6-(2,6-difluorophenyl)imidazo [1,2-a]pyrimidine, 4.85 g of DBU and 29 ml of phosphorus oxychloride was refluxed under heating for 10 hours. The reaction mixture was concentrated, and chloroform and aqueous saturated sodium bicarbonate solution were added to the residue. The separated organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated brine subsequently, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 2.48 g of 5,7-dichloro-6-(2,6-difluorophenyl)imidazo[1,2-a]pyrimidine.

(d) Preparation of 5-(hexamethyleneimin-1-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine

At room temperature, 0.30 g of 5,7-dichloro-6-(2,6-difluorophenyl) imidazo[1,2-a]pyrimidine, 0.79 g of hexamethyleneimine and 0.5 ml of chloroform were mixed. The reaction mixture was subjected to silica gel chromatography to give 0.26 g of 5-(hexamethyleneimin-1-yl)-6-(2,6-difluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine.

The present compounds produced by the above-mentioned methods or the like are given below together with their compound numbers, but the present compounds should not be restricted by the following examples.

Compounds given by formula:

TABLE 1

Com- pound No. R¹R²N Ar R³ 1 NH₂ 2,4,6-F₃-Ph Cl 2 MeNH 2,4,6-F₃-Ph Cl 3 EtNH 2,4,6-F₃-Ph Cl 4 i-PrNH 2,4,6-F₃-Ph Cl 5 BuNH 2,4,6-F₃-Ph Cl 6 Me₂N 2,4,6-F₃-Ph Cl 7 Et₂N 2,4,6-F₃-Ph Cl 8 Pr₂N 2,4,6-F₃-Ph Cl 9 Bu₂N 2,4,6-F₃-Ph Cl 10 (i-Bu)₂N 2,4,6-F₃-Ph Cl 11 (CF₃CH₂)NH 2,4,6-F₃-Ph Cl 12 [CF₃CH(Me)]NH 2,4,6-F₃-Ph Cl 13 (CF₃CH₂)(Me)N 2,4,6-F₃-Ph Cl 14 (CF₃CH₂)(Et)N 2,4,6-F₃-Ph Cl 15 (CF₃CH₂)(CH₂═CHCH₂)N 2,4,6-F₃-Ph Cl 16 (CF₃CH₂)(i-Bu)N 2,4,6-F₃-Ph Cl 17 c-PrNH 2,4,6-F₃-Ph Cl 18 c-BuNH 2,4,6-F₃-Ph Cl 19 c-PentNH 2,4,6-F₃-Ph Cl 20 c-HexNH 2,4,6-F₃-Ph Cl 21 (c-Hex)(Me)N 2,4,6-F₃-Ph Cl 22 (2-Me-c-Hex)NH 2,4,6-F₃-Ph Cl 23 (3-Me-c-Hex)NH 2,4,6-F₃-Ph Cl 24 (4-Me-c-Hex)NH 2,4,6-F₃-Ph Cl 25 c-HepNH 2,4,6-F₃-Ph Cl 26 c-OctNH 2,4,6-F₃-Ph Cl 27 (CH₂═CHCH₂)NH 2,4,6-F₃-Ph Cl 28 [CH₂═C(Me)CH₂]NH 2,4,6-F₃-Ph Cl 29 (CH₂═CHCH₂)₂N 2,4,6-F₃-Ph Cl 30 [CH₂═C(Me)CH₂]₂N 2,4,6-F₃-Ph Cl 31 (CH≡CCH₂)NH 2,4,6-F₃-Ph Cl 32 (CH≡CCH₂)₂N 2,4,6-F₃-Ph Cl 33 (Me₂NCH₂CH₂)NH 2,4,6-F₃-Ph Cl 34 (MeOCH₂CH₂)NH 2,4,6-F₃-Ph Cl 35 (EtOCH₂CH₂)NH 2,4,6-F₃-Ph Cl 36 [(MeO)₂CHCH₂]NH 2,4,6-F₃-Ph Cl 37 [(EtO)₂CHCH₂]NH 2,4,6-F₃-Ph Cl 38 [(MeO)₂CHCH₂](Me)N 2,4,6-F₃-Ph Cl 39 (MeSCH₂CH₂)NH 2,4,6-F₃-Ph Cl 40 (MeSCH₂CH₂)NH 2,4,6-F₃-Ph Cl 41 [(MeOOC)CH₂]NH 2,4,6-F₃-Ph Cl 42 [(EtOOC)CH₂]NH 2,4,6-F₃-Ph Cl 43 (N≡CCH₂)NH 2,4,6-F₃-Ph Cl 44 (N≡CCH₂)(Me)N 2,4,6-F₃-Ph Cl 45 (N≡CCH₂)₂N 2,4,6-F₃-Ph Cl 46 (2-Me-Z1) 2,4,6-F₃-Ph Cl 47 Z2 2,4,6-F₃-Ph Cl 48 Z3 2,4,6-F₃-Ph Cl 49 (2-Me-Z3) 2,4,6-F₃-Ph Cl 50 (2,5-Me₂-Z3) 2,4,6-F₃-Ph Cl 51 Z4 2,4,6-F₃-Ph Cl 52 Z5 2,4,6-F₃-Ph Cl 53 (2-Me-Z5) 2,4,6-F₃-Ph Cl 54 (3-Me-Z5) 2,4,6-F₃-Ph Cl 55 (4-Me-Z5) 2,4,6-F₃-Ph Cl 56 (2-CF₃-Z5) 2,4,6-F₃-Ph Cl 57 (4-CF₃-Z5) 2,4,6-F₃-Ph Cl 58 (3-Cl-Z5) 2,4,6-F₃-Ph Cl 59 (4-Cl-Z5) 2,4,6-F₃-Ph Cl 60 (3-F-Z5) 2,4,6-F₃-Ph Cl 61 (4-F-Z5) 2,4,6-F₃-Ph Cl 62 (3,3-Me₂-Z5) 2,4,6-F₃-Ph Cl 63 (3,5-Me₂-Z5) 2,4,6-F₃-Ph Cl 64 (2,6-Me₂-Z5) 2,4,6-F₃-Ph Cl 65 (2-Et-Z5) 2,4,6-F₃-Ph Cl 66 (3-HO-Z5) 2,4,6-F₃-Ph Cl 67 (4-HO-Z5) 2,4,6-F₃-Ph Cl 68 (2-EtOOC-Z5) 2,4,6-F₃-Ph Cl 69 (3-EtOOC-Z5) 2,4,6-F₃-Ph Cl 70 (4-EtOOC-Z5) 2,4,6-F₃-Ph Cl 71 Z6 2,4,6-F₃-Ph Cl 72 Z7 2,4,6-F₃-Ph Cl 73 (2-Me-Z7) 2,4,6-F₃-Ph Cl 74 Z8 2,4,6-F₃-Ph Cl 75 (2-Me-Z9) 2,4,6-F₃-Ph Cl 76 (4-Me-Z10) 2,4,6-F₃-Ph Cl 77 (4-Ac-Z10) 2,4,6-F₃-Ph Cl 78 (4-EtOOC-Z10) 2,4,6-F₃-Ph Cl 79 (4-t-BuOOC-Z10) 2,4,6-F₃-Ph Cl 80 Z11 2,4,6-F₃-Ph Cl 81 Z12 2,4,6-F₃-Ph Cl 82 (2,6-Me₂-Z12) 2,4,6-F₃-Ph Cl 83 Z13 2,4,6-F₃-Ph Cl 84 Z14 2,4,6-F₃-Ph Cl 85 Z15 2,4,6-F₃-Ph Cl 86 (4-Me-Z15) 2,4,6-F₃-Ph Cl 87 (4-Br-Z15) 2,4,6-F₃-Ph Cl 88 (4-EtOOC-Z15) 2,4,6-F₃-Ph Cl 89 (3,5-Me₂-Z15) 2,4,6-F₃-Ph Cl 90 [3,5-(CF₃)₂-Z15] 2,4,6-F₃-Ph Cl 91 Z16 2,4,6-F₃-Ph Cl 92 [4,5-(NO₂)₂-Z16] 2,4,6-F₃-Ph Cl 93 PhNH 2,4,6-F₃-Ph Cl 94 (Ph)(Me)N 2,4,6-F₃-Ph Cl 95 (4-Me-Ph)NH 2,4,6-F₃-Ph Cl 96 (4-F-Ph)NH 2,4,6-F₃-Ph Cl 97 (4-CF₃-Ph)NH 2,4,6-F₃-Ph Cl 98 (4-Cl-Ph)NH 2,4,6-F₃-Ph Cl 99 (4-Br-Ph)NH 2,4,6-F₃-Ph Cl 100 (4-MeO-Ph)NH 2,4,6-F₃-Ph Cl 101 (4-CF₃O-Ph)NH 2,4,6-F₃-Ph Cl 102 (4-MeS-Ph)NH 2,4,6-F₃-Ph Cl 103 (4-MeOOC-Ph)NH 2,4,6-F₃-Ph Cl 104 (4-Cyano-Ph)NH 2,4,6-F₃-Ph Cl 105 (4-NO₂-Ph)NH 2,4,6-F₃-Ph Cl 106 (PhCH₂)NH 2,4,6-F₃-Ph Cl 107 [PhCH(Me)]NH 2,4,6-F₃-Ph Cl 108 (PhCH₂CH₂)NH 2,4,6-F₃-Ph Cl 109 (PhCH₂)(Me)N 2,4,6-F₃-Ph Cl 110 [(4-Me-Ph)CH₂]NH 2,4,6-F₃-Ph Cl 111 [(4-CF₃-Ph)CH₂]NH 2,4,6-F₃-Ph Cl 112 [(4-F-Ph)CH₂]NH 2,4,6-F₃-Ph Cl 113 [(4-Cl-Ph)CH₂]NH 2,4,6-F₃-Ph Cl 114 [(4-Br-Ph)CH₂]NH 2,4,6-F₃-Ph Cl 115 [(4-MeO-Ph)CH₂]NH 2,4,6-F₃-Ph Cl 116 [(4-CF₃O-Ph)CH₂]NH 2,4,6-F₃-Ph Cl 117 [(4-MeO-Ph)CH₂CH₂]NH 2,4,6-F₃-Ph Cl 118 {[3,4-(MeO)₂-Ph]CH₂CH₂}NH 2,4,6-F₃-Ph Cl 119 [(4-NO₂-Ph)CH₂]NH 2,4,6-F₃-Ph Cl 120 (Z3)NH 2,4,6-F₃-Ph Cl 121 (Z5)NH 2,4,6-F₃-Ph Cl 122 (4-Me-Z10)NH 2,4,6-F₃-Ph Cl 123 (Z12)NH 2,4,6-F₃-Ph Cl 124 (1-EtOOC-Piperidin-4-yl)NH 2,4,6-F₃-Ph Cl 125 (2-Thiazolin-2-yl)NH 2,4,6-F₃-Ph Cl 126 (1-Et-Pyrazol-5-yl)NH 2,4,6-F₃-Ph Cl 127 (1,2,4-Triazol-3-yl)NH 2,4,6-F₃-Ph Cl 128 (3-Me-Isoxazol-5-yl)NH 2,4,6-F₃-Ph Cl 129 (5-Me-Isoxazol-3-yl)NH 2,4,6-F₃-Ph Cl 130 (3-Me-Isothiazol-5-yl)NH 2,4,6-F₃-Ph Cl 131 (Thiazol-2-yl)NH 2,4,6-F₃-Ph Cl 132 (1,3,4-Thiadiazol-2-yl)NH 2,4,6-F₃-Ph Cl 133 (Pyridin-2-yl)NH 2,4,6-F₃-Ph Cl 134 (Pyridin-3-yl)NH 2,4,6-F₃-Ph Cl 135 (Pyridin-4-yl)NH 2,4,6-F₃-Ph Cl 136 (5-Me-Pyridin-2-yl)NH 2,4,6-F₃-Ph Cl 137 (5-Cl-Pyridin-2-yl)NH 2,4,6-F₃-Ph Cl 138 (5-Br-Pyridin-2-yl)NH 2,4,6-F₃-Ph Cl 139 (6-MeO-Pyridin-3-yl)NH 2,4,6-F₃-Ph Cl 140 (3-Cl-5-CF₃-Pyridin-2-yl)NH 2,4,6-F₃-Ph Cl 141 (5-NO₂-Pyridin-2-yl)NH 2,4,6-F₃-Ph Cl 142 (Pyrimidin-2-yl)NH 2,4,6-F₃-Ph Cl 143 (Pyrimidin-4-yl)NH 2,4,6-F₃-Ph Cl 144 (6-Cl-2-MeS-Pyrimidin-4-yl)NH 2,4,6-F₃-Ph Cl 145 (Pyrazin-2-yl)NH 2,4,6-F₃-Ph Cl 146 (1,2,4-Triazin-3-yl)NH 2,4,6-F₃-Ph Cl 147 (NH₂)NH 2,4,6-F₃-Ph Cl 148 (Me₂N)NH 2,4,6-F₃-Ph Cl 149 (PhNH)NH 2,4,6-F₃-Ph Cl 150 (MeNH)(Me)N 2,4,6-F₃-Ph Cl 151 (MeO)NH 2,4,6-F₃-Ph Cl 152 (EtO)NH 2,4,6-F₃-Ph Cl 153 (t-BuO)NH 2,4,6-F₃-Ph Cl 154 (PhCH₂O)NH 2,4,6-F₃-Ph Cl 155 (MeO)(Me)N 2,4,6-F₃-Ph Cl 156 NH₂ 2-Cl-6-F-Ph Cl 157 MeNH 2-Cl-6-F-Ph Cl 158 EtNH 2-Cl-6-F-Ph Cl 159 i-PrNH 2-Cl-6-F-Ph Cl 160 Me₂N 2-Cl-6-F-Ph Cl 161 Et₂N 2-Cl-6-F-Ph Cl 162 Pr₂N 2-Cl-6-F-Ph Cl 163 Bu₂N 2-Cl-6-F-Ph Cl 164 (i-Bu)₂N 2-Cl-6-F-Ph Cl 165 (CF₃CH₂)NH 2-Cl-6-F-Ph Cl 166 [CF₃CH(Me)]NH 2-Cl-6-F-Ph Cl 167 c-PentNH 2-Cl-6-F-Ph Cl 168 c-HexNH 2-Cl-6-F-Ph Cl 169 (c-Hex)(Me)N 2-Cl-6-F-Ph Cl 170 (CH₂═CHCH₂)NH 2-Cl-6-F-Ph Cl 171 (CH₂═CHCH₂)₂N 2-Cl-6-F-Ph Cl 172 [CH₂═C(Me)CH₂]₂N 2-Cl-6-F-Ph Cl 173 (CH≡CCH₂)NH 2-Cl-6-F-Ph Cl 174 (CH≡CCH₂)₂N 2-Cl-6-F-Ph Cl 175 Z3 2-Cl-6-F-Ph Cl 176 (2-Me-Z3) 2-Cl-6-F-Ph Cl 177 (2,5-Me₂-Z3) 2-Cl-6-F-Ph Cl 178 Z4 2-Cl-6-F-Ph Cl 179 Z5 2-Cl-6-F-Ph Cl 180 (2-Me-Z5) 2-Cl-6-F-Ph Cl 181 (3-Me-Z5) 2-Cl-6-F-Ph Cl 182 (4-Me-Z5) 2-Cl-6-F-Ph Cl 183 (3,3-Me₂-Z5) 2-Cl-6-F-Ph Cl 184 (3,5-Me₂-Z5) 2-Cl-6-F-Ph Cl 185 (2,6-Me₂-Z5) 2-Cl-6-F-Ph Cl 186 Z6 2-Cl-6-F-Ph Cl 187 Z7 2-Cl-6-F-Ph Cl 188 (2-Me-Z7) 2-Cl-6-F-Ph Cl 189 Z8 2-Cl-6-F-Ph Cl 190 (4-Me-Z10) 2-Cl-6-F-Ph Cl 191 Z11 2-Cl-6-F-Ph Cl 192 Z12 2-Cl-6-F-Ph Cl 193 (2,6-Me₂-Z12) 2-Cl-6-F-Ph Cl 194 Z13 2-Cl-6-F-Ph Cl 195 Z14 2-Cl-6-F-Ph Cl 196 Z15 2-Cl-6-F-Ph Cl 197 Z16 2-Cl-6-F-Ph Cl 198 PhNH 2-Cl-6-F-Ph Cl 199 (Ph)(Me)N 2-Cl-6-F-Ph Cl 200 (PhCH₂)NH 2-Cl-6-F-Ph Cl 201 (PhCH₂)(Me)N 2-Cl-6-F-Ph Cl 202 NH₂ 2,6-F₂-Ph Cl 203 MeNH 2,6-F₂-Ph Cl 204 EtNH 2,6-F₂-Ph Cl 205 i-PrNH 2,6-F₂-Ph Cl 206 Me₂N 2,6-F₂-Ph Cl 207 Et₂N 2,6-F₂-Ph Cl 208 Pr₂N 2,6-F₂-Ph Cl 209 Bu₂N 2,6-F₂-Ph Cl 210 (i-Bu)₂N 2,6-F₂-Ph Cl 211 (CF₃CH₂)NH 2,6-F₂-Ph Cl 212 [CF₃CH(Me)]NH 2,6-F₂-Ph Cl 213 c-PentNH 2,6-F₂-Ph Cl 214 c-HexNH 2,6-F₂-Ph Cl 215 (c-Hex)(Me)N 2,6-F₂-Ph Cl 216 (CH₂═CHCH₂)NH 2,6-F₂-Ph Cl 217 (CH₂═CHCH₂)₂N 2,6-F₂-Ph Cl 218 [CH₂═C(Me)CH₂]₂N 2,6-F₂-Ph Cl 219 (CH≡CCH₂)NH 2,6-F₂-Ph Cl 220 (CH≡CCH₂)₂N 2,6-F₂-Ph Cl 221 Z3 2,6-F₂-Ph Cl 222 (2-Me-Z3) 2,6-F₂-Ph Cl 223 (2,5-Me₂-Z3) 2,6-F₂-Ph Cl 224 Z4 2,6-F₂-Ph Cl 225 Z5 2,6-F₂-Ph Cl 226 (2-Me-Z5) 2,6-F₂-Ph Cl 227 (3-Me-Z5) 2,6-F₂-Ph Cl 228 (4-Me-Z5) 2,6-F₂-Ph Cl 229 (3,3-Me₂-Z5) 2,6-F₂-Ph Cl 230 (3,5-Me₂-Z5) 2,6-F₂-Ph Cl 231 (2,6-Me₂-Z5) 2,6-F₂-Ph Cl 232 Z6 2,6-F₂-Ph Cl 233 Z7 2,6-F₂-Ph Cl 234 (2-Me-Z7) 2,6-F₂-Ph Cl 235 Z8 2,6-F₂-Ph Cl 236 (4-Me-Z10) 2,6-F₂-Ph Cl 237 Z11 2,6-F₂-Ph Cl 238 Z12 2,6-F₂-Ph Cl 239 (2,6-Me₂-Z12) 2,6-F₂-Ph Cl 240 Z13 2,6-F₂-Ph Cl 241 Z14 2,6-F₂-Ph Cl 242 Z15 2,6-F₂-Ph Cl 243 Z16 2,6-F₂-Ph Cl 244 PhNH 2,6-F₂-Ph Cl 245 (Ph)(Me)N 2,6-F₂-Ph Cl 246 (PhCH₂)NH 2,6-F₂-Ph Cl 247 (PhCH₂)(Me)N 2,6-F₂-Ph Cl 248 Z5 Ph Cl 249 (4-Me-Z5) Ph Cl 250 (2-Me-Z5) Ph Cl 251 Z7 Ph Cl 252 Z5 2-Cl-Ph Cl 253 (4-Me-Z5) 2-Cl-Ph Cl 254 (2-Me-Z5) 2-Cl-Ph Cl 255 Z7 2-Cl-Ph Cl 256 Z5 2-F-Ph Cl 257 (4-Me-Z5) 2-F-Ph Cl 258 (2-Me-Z5) 2-F-Ph Cl 259 Z7 2-F-Ph Cl 260 Z5 2-Me-Ph Cl 261 (4-Me-Z5) 2-Me-Ph Cl 262 (2-Me-Z5) 2-Me-Ph Cl 263 Z7 2-Me-Ph Cl 264 Z5 2-CF₃-Ph Cl 265 (4-Me-Z5) 2-CF₃-Ph Cl 266 (2-Me-Z5) 2-CF₃-Ph Cl 267 Z7 2-CF₃-Ph Cl 268 Z5 3-Cl-Ph Cl 269 (4-Me-Z5) 3-Cl-Ph Cl 270 (2-Me-Z5) 3-Cl-Ph Cl 271 Z7 3-Cl-Ph Cl 272 Z5 3-F-Ph Cl 273 (4-Me-Z5) 3-F-Ph Cl 274 (2-Me-Z5) 3-F-Ph Cl 275 Z7 3-F-Ph Cl 276 Z5 4-Cl-Ph Cl 277 (4-Me-Z5) 4-Cl-Ph Cl 278 (2-Me-Z5) 4-Cl-Ph Cl 279 Z7 4-Cl-Ph Cl 280 Z5 4-F-Ph Cl 281 (4-Me-Z5) 4-F-Ph Cl 282 (2-Me-Z5) 4-F-Ph Cl 283 Z7 4-F-Ph Cl 284 Z5 2,6-Cl₂-Ph Cl 285 (4-Me-Z5) 2,6-Cl₂-Ph Cl 286 (2-Me-Z5) 2,6-Cl₂-Ph Cl 287 Z7 2,6-Cl₂-Ph Cl 288 Z5 2,4-Cl₂-Ph Cl 289 (4-Me-Z5) 2,4-Cl₂-Ph Cl 290 (2-Me-Z5) 2,4-Cl₂-Ph Cl 291 Z7 2,4-Cl₂-Ph Cl 292 Z5 2,4-F₂-Ph Cl 293 (4-Me-Z5) 2,4-F₂-Ph Cl 294 (2-Me-Z5) 2,4-F₂-Ph Cl 295 Z7 2,4-F₂-Ph Cl 296 Z5 3,5-Cl₂-Ph Cl 297 (4-Me-Z5) 3,5-Cl₂-Ph Cl 298 (2-Me-Z5) 3,5-Cl₂-Ph Cl 299 Z7 3,5-Cl₂-Ph Cl 300 Z5 3,5-F₂-Ph Cl 301 (4-Me-Z5) 3,5-F₂-Ph Cl 302 (2-Me-Z5) 3,5-F₂-Ph Cl 303 Z7 3,5-F₂-Ph Cl 304 Z5 2,4,6-Cl₃-Ph Cl 305 (4-Me-Z5) 2,4,6-Cl₃-Ph Cl 306 (2-Me-Z5) 2,4,6-Cl₃-Ph Cl 307 Z7 2,4,6-Cl₃-Ph Cl 308 Z5 2,6-Cl₂-4-F-Ph Cl 309 (4-Me-Z5) 2,6-Cl₂-4-F-Ph Cl 310 (2-Me-Z5) 2,6-Cl₂-4-F-Ph Cl 311 Z7 2,6-Cl₂-4-F-Ph Cl 312 Z5 2,4-Cl₂-6-F-Ph Cl 313 (4-Me-Z5) 2,4-Cl₂-6-F-Ph Cl 314 (2-Me-Z5) 2,4-Cl₂-6-F-Ph Cl 315 Z7 2,4-Cl₂-6-F-Ph Cl 316 Z5 2-Cl-4,6-F₂-Ph Cl 317 (4-Me-Z5) 2-Cl-4,6-F₂-Ph Cl 318 (2-Me-Z5) 2-Cl-4,6-F₂-Ph Cl 319 Z7 2-Cl-4,6-F₂-Ph Cl 320 Z5 4-Cl-2,6-F₂-Ph Cl 321 (4-Me-Z5) 4-Cl-2,6-F₂-Ph Cl 322 (2-Me-Z5) 4-Cl-2,6-F₂-Ph Cl 323 Z7 4-Cl-2,6-F₂-Ph Cl 324 Z5 2,6-F₂-4-(MeO)-Ph Cl 325 (4-Me-Z5) 2,6-F₂-4-(MeO)-Ph Cl 326 (2-Me-Z5) 2,6-F₂-4-(MeO)-Ph Cl 327 Z7 2,6-F₂-4-(MeO)-Ph Cl 328 Z5 2,3,6-F₃-Ph Cl 329 (4-Me-Z5) 2,3,6-F₃-Ph Cl 330 (2-Me-Z5) 2,3,6-F₃-Ph Cl 331 Z7 2,3,6-F₃-Ph Cl 332 Z5 2,3,4,5,6-F₅-Ph Cl 333 (4-Me-Z5) 2,3,4,5,6-F₅-Ph Cl 334 (2-Me-Z5) 2,3,4,5,6-F₅-Ph Cl 335 Z7 2,3,4,5,6-F₅-Ph Cl 336 Z5 3-F-6-CF₃-Ph Cl 337 (4-Me-Z5) 3-F-6-CF₃-Ph Cl 338 (2-Me-Z5) 3-F-6-CF₃-Ph Cl 339 Z7 3-F-6-CF₃-Ph Cl 340 Z5 2,4,6-Me₃-Ph Cl 341 (4-Me-Z5) 2,4,6-Me₃-Ph Cl 342 (2-Me-Z5) 2,4,6-Me₃-Ph Cl 343 Z7 2,4,6-Me₃-Ph Cl 344 NH₂ 2,4,6-F₃-Ph Me 345 MeNH 2,4,6-F₃-Ph Me 346 EtNH 2,4,6-F₃-Ph Me 347 i-PrNH 2,4,6-F₃-Ph Me 348 Me₂N 2,4,6-F₃-Ph Me 349 Et₂N 2,4,6-F₃-Ph Me 350 Pr₂N 2,4,6-F₃-Ph Me 351 Bu₂N 2,4,6-F₃-Ph Me 352 (i-Bu)₂N 2,4,6-F₃-Ph Me 353 (CF₃CH₂)NH 2,4,6-F₃-Ph Me 354 [CF₃CH(Me)]NH 2,4,6-F₃-Ph Me 355 c-PentNH 2,4,6-F₃-Ph Me 356 c-HexNH 2,4,6-F₃-Ph Me 357 (c-Hex)(Me)N 2,4,6-F₃-Ph Me 358 (CH₂═CHCH₂)NH 2,4,6-F₃-Ph Me 359 (CH₂═CHCH₂)₂N 2,4,6-F₃-Ph Me 360 [CH₂═C(Me)CH₂]₂N 2,4,6-F₃-Ph Me 361 (CH≡CCH₂)NH 2,4,6-F₃-Ph Me 362 (CH≡CCH₂)₂N 2,4,6-F₃-Ph Me 363 Z3 2,4,6-F₃-Ph Me 364 (2-Me-Z3) 2,4,6-F₃-Ph Me 365 (2,5-Me₂-Z3) 2,4,6-F₃-Ph Me 366 Z4 2,4,6-F₃-Ph Me 367 Z5 2,4,6-F₃-Ph Me 368 (2-Me-Z5) 2,4,6-F₃-Ph Me 369 (3-Me-Z5) 2,4,6-F₃-Ph Me 370 (4-Me-Z5) 2,4,6-F₃-Ph Me 371 (3,3-Me₂-Z5) 2,4,6-F₃-Ph Me 372 (3,5-Me₂-Z5) 2,4,6-F₃-Ph Me 373 (2,6-Me₂-Z5) 2,4,6-F₃-Ph Me 374 Z6 2,4,6-F₃-Ph Me 375 Z7 2,4,6-F₃-Ph Me 376 (2-Me-Z7) 2,4,6-F₃-Ph Me 377 Z8 2,4,6-F₃-Ph Me 378 (4-Me-Z10) 2,4,6-F₃-Ph Me 379 Z11 2,4,6-F₃-Ph Me 380 Z12 2,4,6-F₃-Ph Me 381 (2,6-Me₂-Z12) 2,4,6-F₃-Ph Me 382 Z13 2,4,6-F₃-Ph Me 383 Z14 2,4,6-F₃-Ph Me 384 Z15 2,4,6-F₃-Ph Me 385 Z16 2,4,6-F₃-Ph Me 386 PhNH 2,4,6-F₃-Ph Me 387 (Ph)(Me)N 2,4,6-F₃-Ph Me 388 (PhCH₂)NH 2,4,6-F₃-Ph Me 389 (PhCH₂)(Me)N 2,4,6-F₃-Ph Me 390 Z5 2,4,6-F₃-Ph Et 391 (4-Me-Z5) 2,4,6-F₃-Ph Et 392 (2-Me-Z5) 2,4,6-F₃-Ph Et 393 Z7 2,4,6-F₃-Ph Et 394 Z5 2,4,6-F₃-Ph Pr 395 (4-Me-Z5) 2,4,6-F₃-Ph Pr 396 (2-Me-Z5) 2,4,6-F₃-Ph Pr 397 Z7 2,4,6-F₃-Ph Pr 398 Z5 2,4,6-F₃-Ph i-Pr 399 (4-Me-Z5) 2,4,6-F₃-Ph i-Pr 400 (2-Me-Z5) 2,4,6-F₃-Ph i-Pr 401 Z7 2,4,6-F₃-Ph i-Pr 402 NH₂ 2-Cl-6-F-Ph Me 403 MeNH 2-Cl-6-F-Ph Me 404 EtNH 2-Cl-6-F-Ph Me 405 i-PrNH 2-Cl-6-F-Ph Me 406 Me₂N 2-Cl-6-F-Ph Me 407 Et₂N 2-Cl-6-F-Ph Me 408 Pr₂N 2-Cl-6-F-Ph Me 409 Bu₂N 2-Cl-6-F-Ph Me 410 (i-Bu)₂N 2-Cl-6-F-Ph Me 411 (CF₃CH₂)NH 2-Cl-6-F-Ph Me 412 [CF₃CH(Me)]NH 2-Cl-6-F-Ph Me 413 c-PentNH 2-Cl-6-F-Ph Me 414 c-HexNH 2-Cl-6-F-Ph Me 415 (c-Hex)(Me)N 2-Cl-6-F-Ph Me 416 (CH₂═CHCH₂)NH 2-Cl-6-F-Ph Me 417 (CH₂═CHCH₂)₂N 2-Cl-6-F-Ph Me 418 [CH₂═C(Me)CH₂]₂N 2-Cl-6-F-Ph Me 419 (CH≡CCH₂)NH 2-Cl-6-F-Ph Me 420 (CH≡CCH₂)₂N 2-Cl-6-F-Ph Me 421 Z3 2-Cl-6-F-Ph Me 422 (2-Me-Z3) 2-Cl-6-F-Ph Me 423 (2,5-Me₂-Z3) 2-Cl-6-F-Ph Me 424 Z4 2-Cl-6-F-Ph Me 425 Z5 2-Cl-6-F-Ph Me 426 (2-Me-Z5) 2-Cl-6-F-Ph Me 427 (3-Me-Z5) 2-Cl-6-F-Ph Me 428 (4-Me-Z5) 2-Cl-6-F-Ph Me 429 (3,3-Me₂-Z5) 2-Cl-6-F-Ph Me 430 (3,5-Me₂-Z5) 2-Cl-6-F-Ph Me 431 (2,6-Me₂-Z5) 2-Cl-6-F-Ph Me 432 Z6 2-Cl-6-F-Ph Me 433 Z7 2-Cl-6-F-Ph Me 434 (2-Me-Z7) 2-Cl-6-F-Ph Me 435 Z8 2-Cl-6-F-Ph Me 436 (4-Me-Z10) 2-Cl-6-F-Ph Me 437 Z11 2-Cl-6-F-Ph Me 438 Z12 2-Cl-6-F-Ph Me 439 (2,6-Me₂-Z12) 2-Cl-6-F-Ph Me 440 Z13 2-Cl-6-F-Ph Me 441 Z14 2-Cl-6-F-Ph Me 442 Z15 2-Cl-6-F-Ph Me 443 Z16 2-Cl-6-F-Ph Me 444 PhNH 2-Cl-6-F-Ph Me 445 (Ph)(Me)N 2-Cl-6-F-Ph Me 446 (PhCH₂)NH 2-Cl-6-F-Ph Me 447 (PhCH₂)(Me)N 2-Cl-6-F-Ph Me 448 Z5 2-Cl-6-F-Ph Et 449 (4-Me-Z5) 2-Cl-6-F-Ph Et 450 (2-Me-Z5) 2-Cl-6-F-Ph Et 451 Z7 2-Cl-6-F-Ph Et 452 Z5 2-Cl-6-F-Ph Pr 453 (4-Me-Z5) 2-Cl-6-F-Ph Pr 454 (2-Me-Z5) 2-Cl-6-F-Ph Pr 455 Z7 2-Cl-6-F-Ph Pr 456 Z5 2-Cl-6-F-Ph i-Pr 457 (4-Me-Z5) 2-Cl-6-F-Ph i-Pr 458 (2-Me-Z5) 2-Cl-6-F-Ph i-Pr 459 Z7 2-Cl-6-F-Ph i-Pr 460 NH₂ 2,6-F₂-Ph Me 461 MeNH 2,6-F₂-Ph Me 462 EtNH 2,6-F₂-Ph Me 463 i-PrNH 2,6-F₂-Ph Me 464 Me₂N 2,6-F₂-Ph Me 465 Et₂N 2,6-F₂-Ph Me 466 Pr₂N 2,6-F₂-Ph Me 467 Bu₂N 2,6-F₂-Ph Me 468 (i-Bu)₂N 2,6-F₂-Ph Me 469 (CF₃CH₂)NH 2,6-F₂-Ph Me 470 [CF₃CH(Me)]NH 2,6-F₂-Ph Me 471 c-PentNH 2,6-F₂-Ph Me 472 c-HexNH 2,6-F₂-Ph Me 473 (c-Hex)(Me)N 2,6-F₂-Ph Me 474 (CH₂═CHCH₂)NH 2,6-F₂-Ph Me 475 (CH₂═CHCH₂)₂N 2,6-F₂-Ph Me 476 [CH₂═C(Me)CH₂]₂N 2,6-F₂-Ph Me 477 (CH≡CCH₂)NH 2,6-F₂-Ph Me 478 (CH≡CCH₂)₂N 2,6-F₂-Ph Me 479 Z3 2,6-F₂-Ph Me 480 (2-Me-Z3) 2,6-F₂-Ph Me 481 (2,5-Me₂-Z3) 2,6-F₂-Ph Me 482 Z4 2,6-F₂-Ph Me 483 Z5 2,6-F₂-Ph Me 484 (2-Me-Z5) 2,6-F₂-Ph Me 485 (3-Me-Z5) 2,6-F₂-Ph Me 486 (4-Me-Z5) 2,6-F₂-Ph Me 487 (3,3-Me₂-Z5) 2,6-F₂-Ph Me 488 (3,5-Me₂-Z5) 2,6-F₂-Ph Me 489 (2,6-Me₂-Z5) 2,6-F₂-Ph Me 490 Z6 2,6-F₂-Ph Me 491 Z7 2,6-F₂-Ph Me 492 (2-Me-Z7) 2,6-F₂-Ph Me 493 Z8 2,6-F₂-Ph Me 494 (4-Me-Z10) 2,6-F₂-Ph Me 495 Z11 2,6-F₂-Ph Me 496 Z12 2,6-F₂-Ph Me 497 (2,6-Me₂-Z12) 2,6-F₂-Ph Me 498 Z13 2,6-F₂-Ph Me 499 Z14 2,6-F₂-Ph Me 500 Z15 2,6-F₂-Ph Me 501 Z16 2,6-F₂-Ph Me 502 PhNH 2,6-F₂-Ph Me 503 (Ph)(Me)N 2,6-F₂-Ph Me 504 (PhCH₂)NH 2,6-F₂-Ph Me 505 (PhCH₂)(Me)N 2,6-F₂-Ph Me 506 Z5 2,6-F₂-Ph Et 507 (4-Me-Z5) 2,6-F₂-Ph Et 508 (2-Me-Z5) 2,6-F₂-Ph Et 509 Z7 2,6-F₂-Ph Et 510 Z5 2,6-F₂-Ph Pr 511 (4-Me-Z5) 2,6-F₂-Ph Pr 512 (2-Me-Z5) 2,6-F₂-Ph Pr 513 Z7 2,6-F₂-Ph Pr 514 Z5 2,6-F₂-Ph i-Pr 515 (4-Me-Z5) 2,6-F₂-Ph i-Pr 516 (2-Me-Z5) 2,6-F₂-Ph i-Pr 517 Z7 2,6-F₂-Ph i-Pr 518 Z17 2,4,6-F₃-Ph Cl 519 Z18 2,4,6-F₃-Ph Cl 520 Z19 2,4,6-F₃-Ph Cl 521 Z20 2,4,6-F₃-Ph Cl 522 Z21 2,4,6-F₃-Ph Cl 523 Z22 2,4,6-F₃-Ph Cl 524 Z23 2,4,6-F₃-Ph Cl 525 Z24 2,4,6-F₃-Ph Cl 526 Z25 2,4,6-F₃-Ph Cl 527 Z26 2,4,6-F₃-Ph Cl 528 Z27 2,4,6-F₃-Ph Cl 529 Z28 2,4,6-F₃-Ph Cl 530 Z29 2,4,6-F₃-Ph Cl 531 Z30 2,4,6-F₃-Ph Cl 532 Z31 2,4,6-F₃-Ph Cl 533 (Et)(Me)N 2,4,6-F₃-Ph Cl 534 (Pr)(Me)N 2,4,6-F₃-Ph Cl 535 (Bu)(Me)N 2,4,6-F₃-Ph Cl 536 (CH₂═CHCH₂)(Me)N 2,4,6-F₃-Ph Cl 537 (CH≡CHCH₂)(Me)N 2,4,6-F₃-Ph Cl 538 Z17 2-Cl-6-F-Ph Cl 539 Z18 2-Cl-6-F-Ph Cl 540 Z19 2-Cl-6-F-Ph Cl 541 Z20 2-Cl-6-F-Ph Cl 542 Z21 2-Cl-6-F-Ph Cl 543 Z22 2-Cl-6-F-Ph Cl 544 Z23 2-Cl-6-F-Ph Cl 545 Z24 2-Cl-6-F-Ph Cl 546 Z25 2-Cl-6-F-Ph Cl 547 Z26 2-Cl-6-F-Ph Cl 548 Z27 2-Cl-6-F-Ph Cl 549 Z28 2-Cl-6-F-Ph Cl 550 Z29 2-Cl-6-F-Ph Cl 551 Z30 2-Cl-6-F-Ph Cl 552 Z31 2-Cl-6-F-Ph Cl 553 (Et)(Me)N 2-Cl-6-F-Ph Cl 554 (Pr)(Me)N 2-Cl-6-F-Ph Cl 555 (Bu)(Me)N 2-Cl-6-F-Ph Cl 556 (CH₂═CHCH₂)(Me)N 2-Cl-6-F-Ph Cl 557 (CH≡CHCH₂)(Me)N 2-Cl-6-F-Ph Cl 558 Z17 2,6-F₂-Ph Cl 559 Z18 2,6-F₂-Ph Cl 560 Z19 2,6-F₂-Ph Cl 561 Z20 2,6-F₂-Ph Cl 562 Z21 2,6-F₂-Ph Cl 563 Z22 2,6-F₂-Ph Cl 564 Z23 2,6-F₂-Ph Cl 565 Z24 2,6-F₂-Ph Cl 566 Z25 2,6-F₂-Ph Cl 567 Z26 2,6-F₂-Ph Cl 568 Z27 2,6-F₂-Ph Cl 569 Z28 2,6-F₂-Ph Cl 570 Z29 2,6-F₂-Ph Cl 571 Z30 2,6-F₂-Ph Cl 572 Z31 2,6-F₂-Ph Cl 573 (Et)(Me)N 2,6-F₂-Ph Cl 574 (Pr)(Me)N 2,6-F₂-Ph Cl 575 (Bu)(Me)N 2,6-F₂-Ph Cl 576 (CH₂═CHCH₂)(Me)N 2,6-F₂-Ph Cl 577 (CH≡CHCH₂)(Me)N 2,6-F₂-Ph Cl 578 Z17 2,4,6-F₃-Ph Me 579 Z18 2,4,6-F₃-Ph Me 580 Z19 2,4,6-F₃-Ph Me 581 Z20 2,4,6-F₃-Ph Me 582 Z21 2,4,6-F₃-Ph Me 583 Z22 2,4,6-F₃-Ph Me 584 Z23 2,4,6-F₃-Ph Me 585 Z24 2,4,6-F₃-Ph Me 586 Z25 2,4,6-F₃-Ph Me 587 Z26 2,4,6-F₃-Ph Me 588 Z27 2,4,6-F₃-Ph Me 589 Z28 2,4,6-F₃-Ph Me 590 Z29 2,4,6-F₃-Ph Me 591 Z30 2,4,6-F₃-Ph Me 592 Z31 2,4,6-F₃-Ph Me 593 (Et)(Me)N 2,4,6-F₃-Ph Me 594 (Pr)(Me)N 2,4,6-F₃-Ph Me 595 (Bu)(Me)N 2,4,6-F₃-Ph Me 596 (CH₂═CHCH₂)(Me)N 2,4,6-F₃-Ph Me 597 (CH≡CHCH₂)(Me)N 2,4,6-F₃-Ph Me 598 Z17 2-Cl-6-F-Ph Me 599 Z18 2-Cl-6-F-Ph Me 600 Z19 2-Cl-6-F-Ph Me 601 Z20 2-Cl-6-F-Ph Me 602 Z21 2-Cl-6-F-Ph Me 603 Z22 2-Cl-6-F-Ph Me 604 Z23 2-Cl-6-F-Ph Me 605 Z24 2-Cl-6-F-Ph Me 606 Z25 2-Cl-6-F-Ph Me 607 Z26 2-Cl-6-F-Ph Me 608 Z27 2-Cl-6-F-Ph Me 609 Z28 2-Cl-6-F-Ph Me 610 Z29 2-Cl-6-F-Ph Me 611 Z30 2-Cl-6-F-Ph Me 612 Z31 2-Cl-6-F-Ph Me 613 (Et)(Me)N 2-Cl-6-F-Ph Me 614 (Pr)(Me)N 2-Cl-6-F-Ph Me 615 (Bu)(Me)N 2-Cl-6-F-Ph Me 616 (CH₂═CHCH₂)(Me)N 2-Cl-6-F-Ph Me 617 (CH≡CHCH₂)(Me)N 2-Cl-6-F-Ph Me 618 Z17 2,6-F₂-Ph Me 619 Z18 2,6-F₂-Ph Me 620 Z19 2,6-F₂-Ph Me 621 Z20 2,6-F₂-Ph Me 622 Z21 2,6-F₂-Ph Me 623 Z22 2,6-F₂-Ph Me 624 Z23 2,6-F₂-Ph Me 625 Z24 2,6-F₂-Ph Me 626 Z25 2,6-F₂-Ph Me 627 Z26 2,6-F₂-Ph Me 628 Z27 2,6-F₂-Ph Me 629 Z28 2,6-F₂-Ph Me 630 Z29 2,6-F₂-Ph Me 631 Z30 2,6-F₂-Ph Me 632 Z31 2,6-F₂-Ph Me 633 (Et)(Me)N 2,6-F₂-Ph Me 634 (Pr)(Me)N 2,6-F₂-Ph Me 635 (Bu)(Me)N 2,6-F₂-Ph Me 636 (CH₂═CHCH₂)(Me)N 2,6-F₂-Ph Me 637 (CH≡CHCH₂)(Me)N 2,6-F₂-Ph Me

In the above table, Me, Et, i-Pr, Bu, t-Bu, i-Bu, c-Pr, c-Bu, c-Pent, c-Hex, c-Hep, c-Oct, Ac, Ph and Cyano represents methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, acetyl, phenyl and cyano groups, respectively.

Further, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13, Z14, Z15, Z16, Z17, Z18, Z19, Z20, Z21, Z22, Z23, Z24, Z25, Z26, Z27, Z28, Z29, Z30 and Z31 mean the following groups:

The physical properties of some of the present compounds are given below:

Compound 1

¹H-NMR δ(ppm; TMS): (DMSO-d₆) 7.38 (2H, dd, J=7.6,9.2), 7.58 (1H, d, J=1.6), 7.93 (2H, brs), 7.98 (1H, d, J=1.6)

Compound 4

¹H-NMR δ(ppm; TMS): (CDCl₃) 1.21 (6H, d, J=6.4 Hz), 3.6–3.8 (1H, m), 5.19 (1H, brs), 6.86 (2H, t, J=8.5 Hz), 7.71 (1H, d, J=1 Hz), 7.89 (1H, d, J=1 Hz)

Compound 7

mp: 137.8° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 1.10 (6H, t, J=7.1 Hz), 3.11 (4H, q, J=7.1 Hz), 6.8–6.9 (2H, m), 7.47 (1H, d, J=1.4 Hz), 7.76 (1H, d, J=1.4 Hz)

Compound 8

mp: 95.4° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 0.83 (6H, t, J=7 Hz), 1.4–1.6 (4H, m), 2.9–3.0 (4H, m), 6.84 (2H, dd, J=7.1 Hz,8.5 Hz), 7.48 (1H, d, J=1.3 Hz), 7.76 (1, H, d, J=1.3 Hz)

Compound 9

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.86 (6H, t, J=7.4 Hz), 1.1–1.3 (4H, m), 1.4–1.5 (4H, m), 2.9–3.0 (4H, m), 6.84. (2H, dd, J=7.1 Hz,8.6 Hz), 7.46 (1H, d, J=1.4 Hz), 7.74 (1H, d, J=1.4 Hz)

Compound 20

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.0–2.0 (10H, m), 3.28 (1H, brs), 5.23 (1H, brs), 6.87 (2H, dd, J=6.9 Hz,8.5 Hz), 7.70 (1H, d, J=1 Hz), 7.83 (1H, d, J=1 Hz)

Compound 21

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.9–1.3 (3H, m), 1.4–1.7 (6H, m), 2.72 (3H, s), 3.0–3.2 (1H, m), 6.8–6.9 (2H, m), 7.41 (1H, d, J=1 Hz), 7.76 (1H, d, J=1 Hz)

Compound 29

¹H-NMR δ (ppm; TMS): (CDCl₃) 3.62 (4H, d, J=6.0 Hz), 5.1–5.3 (4H, m), 5.5–5.7 (2H, m), 6.85 (2H, dd, J=7.0 Hz,8.5 Hz), 7.51 (1H, d, J=1.4 Hz), 7.76 (1H, d, J=1.4 Hz)

Compound 48

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.8–2.0 (4H, m), 3.2–3.3 (4H, m), 6.81 (2H, dd, J=7.0 Hz,8.4 Hz), 7.53 (1H, d, J=1.4 Hz), 7.69 (1H, d, J=1.7 Hz)

Compound 49

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.98 (3H, d, J=6.0 Hz), 14–1.6 (1H, m), 1.7–1.9 (1H, m), 1.9–2.2 (2H, m), 3.1–3.3 (1H.m), 3.4–3.6 (2H, m), 6.7–6.9 (2H, m), 7.51 (1H, d, J=1.4 Hz), 7.71 (1H, d, J=1.7 Hz)

Compound 50

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.05 (6H, d, J=6.3 Hz), 1.5–1.7 (2H, m), 1.7–1.9 (2H, m), 3.2–3.4 (2H.m), 6.8–6.9 (2H, m), 7.72 (1H, d, J=1.4 Hz), 7.92 (1H, d, J=1.4 Hz)

Compound 52

mp: 174.4° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 1.61 (6H, brs), 2.92 (4H, brs), 6.8–6.9 (2H, m), 7.39 (1H, s), 7.74 (1H, s)

Compound 53

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.03 (3H, d, J=6.5 Hz),1.2–1.8 (6H, m),2.97–3.4 (3H, m), 6.8–6.9 (2H, m),7.53 (1H, br),7.74 (1H, d, J=1.4 Hz)

Compound 54

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.86 (3H, d, J=6.63 Hz), 1.1–1.3 (2H, m), 1.4–1.6 (1H, m), 1.6–1.7 (2H, m), 2.5–2.7 (2H, m), 3.2–3.4 (2H, m), 7.04 (2H, dd, J=7.3 Hz, 8.5 Hz), 7.40 (1H, d, J=1.2 Hz), 7.74 (1H, d, J=1.4 Hz)

Compound 55

mp: 200.8° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 0.99 (3H, d, J=6.4 Hz), 1.1–1.4 (2H, m), 1.4–1.6 (1H, m), 1.6–1.8 (2H, m), 2.5–2.7 (2H, m), 3.2–3.4 (2H, m), 6.85 (2H, dd, J=7.1 Hz,8.4 Hz), 7.40 (1H, d, J=1.7 Hz), 7.77 (1H, d, J=1.7 Hz)

Compound 63

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.6–0.8 (2H, m), 0.82 (6H, d, J=6.6 Hz), 1.7–1.9 (2H, m), 2.0–2.3 (2H, m), 3.2–3.3 (2H, m), 6.85 (2H, dd, J=7.2 Hz,8.3 Hz), 7.37 (1H, d, J=1 Hz), 7.74 (1H, d, J=1 Hz)

Compound 65

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.72 (3H, t, J=7.2 Hz), 1.0–1.8 (8H, m), 3.0–3.4 (3H, m), 6.8–6.9 (2H, m), 7.48 (1H, brs), 7.73 (1H, d, J=1.4 Hz)

Compound 67

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.4–1.9 (2H, m), 1.9–2.0 (2H, m), 2.6–3.0 (2H, m), 3.1–3.4 (2H, m), 3.7–4.1 (1H, m), 6.85, (1H, dd, J=7.0 Hz, 8.2 Hz), 7.39 (1H, d,=1.4 Hz), 7.76 (1H, d, J=1.4 Hz)

Compound 71

¹H-NMR δ (ppm; TMS): (CDCl₃) 2.1–2.4 (2H, m), 3.0–3.3 (2H, m), 3.4–3.7 (2H, m), 5.6–5.7 (1H, m), 5.8–5.9 (1H, m), 6.8–6.9 (2H, m), 7.41 (1H, d, J=1.4 Hz), 7.75 (1H, d, J=1.4 Hz)

Compound 72

mp: 143.8° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 1.6–1.8 (8H, m), 3.1–3.2 (4H, m), 6.85 (2H, dd, J=6.8 Hz, 8.6 Hz), 7.52 (1H, d, J=1 Hz), 7.75 (1H, d, J=1 Hz)

Compound 73

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.7 (10H, m), 3.1–3.2 (4H, m), 6.8–6.9 (2H, m), 7.58 (1H, d, J=1 Hz), 7.77 (1H, d, J=1 Hz)

Compound 76

¹H-NMR δ (ppm; TMS): (CDCl₃) 2.38 (3H, s), 2.57 (4H, brs), 3.07 (4H, brs), 6.85 (2H, dd, J=7.1 Hz,8.4 Hz), 7.44 (1H, d, J=1 Hz), 7.77 (1H, d, J=1 Hz)

Compound 81

mp: 185.4° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 3.01 (4H, brs), 3.77 (4H, t, J=4.6), 6.88 (2H, dd, J=7.1 Hz,8.5 Hz), 7.45 (1H, d, J=1.4 Hz), 7.79 (1H, d, J=1.4 Hz)

Compound 83

mp: 201.7° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 2.68 (4H, brs), 3.23 (4H, brs), 6.8–6.9 (2H, m), 7.45 (1H, d, J=1.4 Hz), 7.80 (1H, d, J=1.4 Hz)

Compound 85

¹H-NMR δ (ppm; TMS): (CDCl₃) 6.44 (1H, t, J=2.4 Hz), 6.76 (2H, dd, J=7.1 Hz,8.5 Hz), 7.43 (1H, d, J=2.6 Hz), 7.72 (1H, d, J=1.6 Hz), 7.85 (1H, d, J=2.6 Hz), 7.86 (1H, d, J=1.6 Hz)

Compound 89

mp: 150.4° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 1.94 (3H, s), 2.20 (3H, s), 5.98 (1H, s), 6.7–6.8 (2H, m), 7.19 (1H, d, J=1.6 Hz), 7.84 (1H, d, J=1.6 Hz)

Compound 90

¹H-NMR δ (ppm; TMS): (CDCl₃) 6.73 (2H, t, J=7.8 Hz),7.02 (1H, d, J=1.4 Hz), 7.12 (1H, s), 7.92 (1H, d, J=1.4 Hz)

Compound 106

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 4.28 (2H, d, J=6.6Hz), 6.8–7.0 (2H, m), 7.07 (2H, dd, J=7.5 Hz,9.1 Hz), 7.68 (1H, d,J=1.5 Hz), 8.19 (1H, d, J=1.5 Hz), 8.4–8.5 (1H, d,m)

Compound 109

¹H-NMR δ (ppm; TMS): (CDCl₃) 2.69 (3H, s), 3.97 (2H, s), 6.87 (2H, dd, J=7.3 Hz,8.4 Hz), 7.2–7.3 (2H, m), 7.3–7.4 (3H, m), 7.48 (1H, d, J=1 Hz), 7.75 (1H, s)

Compound 159

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.17 (6H, t, J=5.5 Hz), 3.6–3.8 (1H, m), 4.74 (1H, brd, J=8.7), 7.1–7.2 (m,1H), 7.3–7.5 (2H, m), 7.72 (2H, s)

Compound 161

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.10 (6H, t, J=7.1 Hz), 3.0–3.2 (4H, m), 7.1–7.2 (1H, m), 7.3–7.5 (2H, m), 7.47 (1H, d, J=1.4 Hz), 7.76 (1H, d, J=1.4 Hz)

Compound 175

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.8–1.9 (4H, m), 3.2–3.3 (4H, m), 7.1–7.2 (m,1H), 7.3–7.5 (m,2H), 7.58 (1H, d, J=1.5 Hz), 7.71 (1H, d, J=1.5 Hz)

Compound 180

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.0–1.8 (9H, m), 2.8–3.4 (3H, m), 7.1–7.2 (1H, m), 7.3–7.7 (3H, m), 7.73 (1H, s)

Compound 182

mp: 183.8° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 0.96 (3H, d, J=6.5 Hz), 1.1–1.3 (2H, m), 1.4–1.6 (1H, m), 1.6–1.7 (2H, m), 2.5–2.7 (2H, m), 3.2–3.4 (2H, m), 7.1–7.2 (1H, m), 7.3–7.5 (2H, m), 7.40 (1H, d, J=1 Hz), 7.78 (1H, d, J=1 Hz)

Compound 187

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.7 (8H, m), 3.1–3.2 (4H, m), 7.16 (1H, dt, J=1.4 Hz, 8.2 Hz), 7.3–7.5 (2H, m), 7.51 (1H, d, J=1.4 Hz), 7.74 (1H, d, J=1.7 Hz)

Compound 226

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.04 (3H, d, J=6.4 Hz), 1.2–1.7 (6H, m), 2.7–3.4 (3H, m), 7.0–7.1 (2H, m), 7.4–7.6 (2H, m), 7.74 (1H, d, J=1.4 Hz)

Compound 228

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.96 (3H, d, J=6.3 Hz), 1.1–1.3 (2H, m), 1.4–1.6 (1H, m), 1.6–1.7 (2H, m), 2.5–2.7 (2H, m), 3.2–3.3 (2H, m), 7.04 (2H, dd, J=7.0 Hz, 8.5 Hz), 7.38 (1H, d, J=1.4 Hz), 7.4–7.5 (1H, m), 7.74 (1H, d, J=1.4 Hz)

Compound 233

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.8 (8H, m), 3.0–3.2 (4H, m), 6.99 (2H, dd, J=7.0 Hz,8.5 Hz), 7.4–7.6 (1H, m), 7.51 (1H, d, J=1.7 Hz), 7.74 (1H, d, J=1.4 Hz)

Compound 249

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.94 (3H, d, J=6.4 Hz), 1.1–1.3 (2H, m), 1.3–1.5 (1H, m), 1.6–1.7 (2H, m), 2.2–2.5 (2H, m), 3.1–3.3 (2H, m), 7.2–7.3 (2H, m), 7.43 (1H, d, J=1 Hz), 7.4–7.6 (3H, m), 7.74 (1H, d, J=1 Hz)

Compound 250

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.8–1.8 (9H, m), 2.1–2.5 (1H, m), 2.7–2.9 (1H, m), 3.1–3.4 (1H, m), 7.2–7.3 (1H, m), 7.3–7.7 (5H, m), 7.73 (1H, s)

Compound 251

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.7 (8H, m), 2.9–3.1 (4H, m), 7.2–7.3 (2H, m), 7.4–7.6 (4H, m), 7.73 (1H, d, J=1.2 Hz)

Compound 253

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.94 (3H, d, J=6.3 Hz), 1.1–1.5 (3H, m), 1.5–1.7 (2H, m), 2.3–2.6 (2H, m), 3.1–3.4 (2H, m), 7.2–7.3 (1H, m), 7.3–7.5 (3H, m), 7.5–7.6 (1H, m), 7.73 (1H, d, J=1.4 Hz)

Compound 255

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.8 (8H, m), 3.0–3.2 (4H, m), 7.23 (1H, dd, J=1.9 Hz, 7.2 Hz), 7.3–7.5 (2H, m), 7.51 (1H, d, J=1.4 Hz), 7.55 (1H, dd, J=1.7 Hz, 7.5 Hz), 7.73 (1H, d, J=1.4 Hz)

Compound 257

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.95 (3H, d, J=6.5 Hz), 1.1–1.4 (2H, m), 1.4–1.7 (3H, m), 2.3–2.6 (2H, m), 3.1–3.4 (2H, m), 7.2–7.3 (3H, m), 7.38 (1H, d, J=1.4 Hz), 7.4–7.5 (1H, m), 7.73 (1H, d, J=1.4 Hz)

Compound 258

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.0–1.2 (3H, m), 1.3–1.8 (4H, m), 2.3–2.8 (2H, m), 2.8–3.5 (3H, m), 7.2–7.6 (5H, m), 7.73 (1H, d, J=1.4 Hz)

Compound 259

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.8 (8H, m), 3.0–3.1 (4H, m), 7.2–7.4 (3H, m), 7.4–7.6 (2H, m), 7.73 (1H, d, J=1.2 Hz)

Compound 261

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.92 (3H, d, J=6.3 Hz), 1.1–1.5 (3H, m), 1.5–1.7 (2H, m), 2.1–2.3 (1H, m), 2.21 (3H, s), 2.5–2.6 (1H, m), 2.8–3.0 (1H, m), 3.3–3.5 (1H, m), 7.03 (1H, d, J=7.5 Hz), 7.2–7.4 (4H, m), 7.73 (1H, d, J=1.4 Hz)

Compound 263

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.4–1.7 (8H, m), 2.9–3.1 (4H, m), 7.04 (1H, dd, J=1.1 Hz,7.5 Hz), 7.2–7.4 (3H, m), 7.51 (1H, d, J=1.4 Hz), 7.74 (1H, d, J=1.4 Hz)

Compound 265

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.93 (3H, d, J=6.5 Hz), 1.1–1.3 (2H, m), 1.3–1.5 (2H, m), 1.5–1.7 (2H, m), 2.2–2.6 (2H, m), 3.2–3.4 (2H, m), 7.3–7.4 (2H, m), 7.6–7.7 (2H, m), 7.7–7.9 (2H, m)

Compound 267

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.4–1.7 (8H, m), 3.0–3.2 (4H, m), 7.31 (1H, d, J=7.5 Hz), 7.49 (1H, d, J=1.4 Hz), 7.6–7.7 (2H, m), 7.73 (1H, d, J=1.7 Hz), 7.82 (1H, d, J=7.5 Hz)

Compound 281

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.95 (3H, d, J=6.5 Hz), 1.1–1.3 (2H, m), 1.3–1.5 (1H, m), 1.6–1.7 (2H, m), 2.3–2.5 (2H, m), 3.1–3.3 (2H, m), 7.1–7.3 (4H, m), 7.37 (1H, d, J=1 Hz), 7.72 (1H, d, J=1H)

Compound 282

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.8–1.1 (3H, m), 1.2–1.8 (6H, m), 2.2–2.8 (2H, m), 3.1–3.5 (1H, m), 7.1–7.7 (5H, m), 7.74 (1H, d, J=1.4 Hz)

Compound 283

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.7 (8H, m), 2.9–3.1 (4H, m), 7.1–7.3 (4H, m), 7.51 (1H, d, J=1.4 Hz), 7.73 (1H, d, J=1.4 Hz)

Compound 285

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.96 (3H, d, J=6.2 Hz), 1.1–1.4 (2H, m), 1.4–1.6 (1H, m), 1.6–1.7 (2H, m), 2.5–2.7 (2H, m), 3.3–3.4 (2H, m), 7.3–7.4 (2H, m), 7.4–7.6 (2H, m), 7.74 (1H, d, J=1 Hz)

Compound 286

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.17 (3H, d, J=6.7 Hz), 1.2–1.7 (6H, m), 3.0–3.7 (3H, m), 7.3–7.4 (1H, m), 7.4–7.6 (3H, m), 7.71 (1H, s)

Compound 287

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.7 (8H, m), 3.1–3.3 (4H, m), 7.3–7.4 (1H, m), 7.4–7.5 (2H, m), 7.51 (1H, d, J=1.4 Hz), 7.74 (1H, d, J=1.4 Hz)

Compound 293

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.97 (3H, d, J=6.3 Hz), 1.2–1.4 (2H, m), 1.4–1.6 (1H, m), 1.6–1.7 (2H, m), 2.4–2.6 (2H, m), 3.1–3.4 (2H, m), 6.9–7.1 (2H, m), 7.1–7.3 (1H, m), 7.38 (1H, d, J=1.4 Hz), 7.74 (1H, d, J=1.4 Hz)

Compound 295

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.8 (8H, m), 3.0–3.1 (4H, m), 6.9–7.1 (2H, m), 7.1–7.3 (1H, m), 7.51 (1H, d, J=1.4 Hz), 7.74 (1H, d, J=1.7 Hz)

Compound 297

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.98 (3H, d, J=6.3 Hz),1.2–1.4 (2H, m), 1.4–1.8 (3H, m), 2.4–2.6 (2H, m), 3.2–3.3 (2H, m), 7.18 (2H, s), 7.4–7.5 (2H, m), 7.74 (1H, d, J=0.7 Hz)

Compound 299

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.5–1.8 (8H, m), 3.0–3.1 (4H, m), 7.20 (2H, d, J=1.4 Hz), 7.4–7.5 (1H, m), 7.51 (1H, d, J=1.2 Hz), 7.75 (1H, d, J=1.2 Hz)

Compound 428

mp: 144.5° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 0.95 (3H, d, J=6.3 Hz), 1.1–1.3 (2H, m), 1.3–1.5 (1H, m), 1.6–1.7 (2H, m), 2.29 (3H, s), 2.4–2.6 (2H, m), 3.2–3.3 (2H, m), 7.1–7.2 (1H, m), 7.3–7.5 (3H, m), 7.76 (1H, d, J=2 Hz)

Compound 449

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.94 (3H, m), 1.20 (3H, t, J=7 Hz), 1.2–1.4 (2H, m), 1.4–1.5 (1H, m), 1.6–1.7 (2H, m), 2.3–2.6 (4H, m), 3.2–3.3 (2H, m), 7.1–7.2 (1H, m), 7.3–7.5 (3H, m), 7.71 (1H, d, J=1.6 Hz)

Compound 518

¹H-NMR δ (ppm; TMS): (CDCl₃) 2.8–3.0 (2H, m), 3.2–3.3 (2H, m), 4.2–4.4 (2H, m), 6.73 (2H, dd, J=7.7 Hz,8.2 Hz), 6.87 (1H, d, J=7.2 Hz), 7.1–7.3 (3H, m), 7.40 (1H, d, J=1 Hz), 7.74 (1H, d, J=1 Hz)

Compound 521

¹H-NMR δ (ppm; TMS): (CDCl₃) 6.5–6.6 (1H, m), 6.7–6.8 (1H, m), 7.06 (1H, d, J=8.3 Hz), 7.12 (1H, d, J=1.5 Hz), 7.3–7.5 (2H, m), 7.8–7.9 (3H, m)

Compound 535

¹H-NMR δ (ppm; TMS): (CDCl₃) 0.86 (3H, d, J=7.3 Hz), 1.2–1.3 (2H, m), 1.4–1.6 (2H, m), 2.7–2.9 (5H, m), 6.84 (2H, dd, J=7.2 Hz,8.5 Hz), 7.44 (1H, d, J=1.4 Hz), 7.74 (1H, d, J=1.4 Hz)

Compound 537

¹H-NMR δ (ppm; TMS): (CDCl₃) 2.41 (1H, t, J=2.4 Hz), 2.75 (3H, s), 3.81 (2H, d, J=2.4 Hz), 6.84 (2H, dd,=7.4 Hz,8.3 Hz), 7.64 (1H, d, J=1.4 Hz), 7.78 (1H, d, J=1.2 Hz)

Further, production intermediates, imidazo[1,2-a]pyrimidine [II], imidazo[1,2-a]pyrimidine [III] and imidazo[1,2-a]pyrimidine [IV] are shown with their compound numbers below.

Compound given by the following formula:

TABLE 2

Compound No. Ar R¹⁰ R¹¹ 2-1 2,4,6-F₃—Ph Cl Cl 2-2 2-Cl-6-F—Ph Cl Cl 2-3 2,6-F₂—Ph Cl Cl 2-4 Ph Cl Cl 2-5 2-Cl—Ph Cl Cl 2-6 2-F—Ph Cl Cl 2-7 2-Me—Ph Cl Cl 2-8 2-CF₃—Ph Cl Cl 2-9 3-Cl—Ph Cl Cl 2-10 3-F—Ph Cl Cl 2-11 4-Cl—Ph Cl Cl 2-12 4-F—Ph Cl Cl 2-13 2,6-Cl₂—Ph Cl Cl 2-14 2,4-Cl₂—Ph Cl Cl 2-15 2,4-F₂—Ph Cl Cl 2-16 3,5-Cl₂—Ph Cl Cl 2-17 3,5-F₂—Ph Cl Cl 2-18 2,4,6-Cl₃—Ph Cl Cl 2-19 2,6-Cl₂-4-F—Ph Cl Cl 2-20 2,4-Cl₂-6-F—Ph Cl Cl 2-21 2-Cl-4,6-F₂—Ph Cl Cl 2-22 4-Cl-2,6-F₂—Ph Cl Cl 2-23 2,6-F₂-4-(MeO)—Ph Cl Cl 2-24 2,3,6-F₃—Ph Cl Cl 2-25 2,3,4,5,6-F₅—Ph Cl Cl 2-26 3-F-6-CF₃—Ph Cl Cl 2-27 2,4,6-Me₃—Ph Cl Cl 2-28 2,4,6-F₃—Ph Cl Me 2-29 2,4,6-F₃—Ph Cl Et 2-30 2,4,6-F₃—Ph Cl Pr 2-31 2,4,6-F₃—Ph Cl i-Pr 2-32 2-Cl-6-F—Ph Cl Me 2-33 2-Cl-6-F—Ph Cl Et 2-34 2-Cl-6-F—Ph Cl Pr 2-35 2-Cl-6-F—Ph Cl i-Pr 2-36 2,6-F₂—Ph Cl Me 2-37 2,6-F₂—Ph Cl Et 2-38 2,6-F₂—Ph Cl Pr 2-39 2,6-F₂—Ph Cl i-Pr 3-1 2,4,6-F₃—Ph OH OH 3-2 2-Cl-6-F—Ph OH OH 3-3 2,6-F₂—Ph OH OH 3-4 Ph OH OH 3-5 2-Cl—Ph OH OH 3-6 2-F—Ph OH OH 3-7 2-Me—Ph OH OH 3-8 2-CF₃—Ph OH OH 3-9 3-Cl—Ph OH OH 3-10 3-F—Ph OH OH 3-11 4-Cl—Ph OH OH 3-12 4-F—Ph OH OH 3-13 2,6-Cl₂—Ph OH OH 3-14 2,4-Cl₂—Ph OH OH 3-15 2,4-F₂—Ph OH OH 3-16 3,5-Cl₂—Ph OH OH 3-17 3,5-F₂—Ph OH OH 3-18 2,4,6-Cl₃—Ph OH OH 3-19 2,6-Cl₂-4-F—Ph OH OH 3-20 2,4-Cl₂-6-F—Ph OH OH 3-21 2-Cl-4,6-F₂—Ph OH OH 3-22 4-Cl-2,6-F₂—Ph OH OH 3-23 2,6-F₂-4-(MeO)—Ph OH OH 3-24 2,3,6-F₃—Ph OH OH 3-25 2,3,4,5,6-F₅—Ph OH OH 3-26 3-F-6-CF₃—Ph OH OH 3-27 2,4,6-Me₃—Ph OH OH 4-1 2,4,6-F₃—Ph OH Me 4-2 2,4,6-F₃—Ph OH Et 4-3 2,4,6-F₃—Ph OH Pr 4-4 2,4,6-F₃—Ph OH i-Pr 4-5 2-Cl-6-F—Ph OH Me 4-6 2-Cl-6-F—Ph OH Et 4-7 2-Cl-6-F—Ph OH Pr 4-8 2-Cl-6-F—Ph OH i-Pr 4-9 2,6-F₂—Ph OH Me 4-10 2,6-F₂—Ph OH Et 4-11 2,6-F₂—Ph OH Pr 4-12 2,6-F₂—Ph OH i-Pr

The physical properties of some of the production intermediates, imidazo[1,2-a]pyrimidine [II], imidazo[1,2-a]pyrimidine [III] and imidazo[1,2-a]pyrimidine [IV] are given below:

Compound 2-1

mp: 192.56° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 6.88 (2H, dd, J=8.6 Hz,7.1 Hz), 7.75 (1H, d, J=1 Hz), 7.92 (1H, d, J=1 Hz)

Compound 2-2

mp: 223.6° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 7.1–7.2 (1H, m), 7.4–7.6 (2H, m), 7.76 (1H, d, J=1 Hz), 7.92 (1H, d, J=1 Hz)

Compound 2-3

¹H-NMR δ (ppm; TMS): (CDCl₃) 7.09 (2H, dd, J=7.5 Hz,8.2 Hz), 7.5–7.6 (1H, m), 7.74 (1H, d, J=1.7 Hz), 7.90 (1H, d, J=1.2 Hz)

Compound 2-4

¹H-NMR δ (ppm; TMS): (CDCl₃) 7.3–7.4 (2H, m), 7.5–7.6 (3H, m), 7.72 (1H, d, J=1.7 Hz), 7.89 (1H, d, J=1.7 Hz)

Compound 2-5

¹H-NMR δ (ppm; TMS): (CDCl₃) 7.32 (1H, dd, J=1.7 Hz,7.6 Hz), 7.4–7.5 (2H, m), 7.58 (1H, dd, J=1.3Hz,7.9 Hz), 7.73 (1H, d, J=1.5 Hz), 7.90 (1H, d, J=1.7 Hz)

Compound 2-6

¹H-NMR δ (ppm; TMS): (CDCl₃) 7.2–7.3 (1H, m), 7.3–7.4 (2H, m), 7.5–7.6 (1H, m), 7.73 (1H, d, J=1.4 Hz), 7.89 (1H, d, J=1.5 Hz)

Compound 2-7

¹H-NMR δ (ppm; TMS): (CDCl₃) 2.15 (3H, s), 7.12 (1H, dd, J=1.0 Hz, 7.6 Hz), 7.3–7.5 (2H, m), 7.72 (1H, d, J=1.7 Hz), 7.90 (1H, d, J=1.7 Hz)

Compound 2-8

¹H-NMR δ (ppm; TMS): (CDCl₃) 7.35 (1H, d, J=7.5 Hz), 7.6–7.8 (2H, m), 7.72 (1H, d, J=1.5 Hz), 7.87 (1H, d, J=7.7 Hz), 7.90 (1H, d, J=1.5 Hz)

Compound 2-12

¹H-NMR δ (ppm; TMS): (CDCl₃) 7.2–7.3 (2H, m), 7.3–7.4 (2H, m), 7.72 (1H, d, J=1.5 Hz), 7.89 (1H, d, J=1.7 Hz)

Compound 2-13

¹H-NMR δ (ppm; TMS): (CDCl3) 7.41–7.46 (1H, m), 7.50–7.53 (2H, m), 7.76 (1H, d, J=1.5 Hz), 7.92 (1H, d, J=1.4 Hz)

Compound 2-15

¹H-NMR δ (ppm; TMS): (CDCl₃) 6.9–7.1 (2H, m), 7.2–7.3 (1H, m), 7.73 (1H, d, J=1.5 Hz), 7.90 (1H, d, J=1.5 Hz)

Compound 2-16

¹H-NMR δ (ppm; TMS): (CDCl₃)7.2–7.3 (2H, m), 7.52 (1H, dt, J=0.5 Hz, 1.9 Hz), 7.73 (1H, d, J=1 Hz), 7.91 (1H, d, J=1.2 Hz)

Compound 2-32

mp: 244.6° C. ¹H-NMR δ (ppm; TMS): (CDCl₃) 2.43 (3H, s), 7.24 (1H, t, J=8 Hz), 7.4–7.6 (2H, m), 7.71 (1H, s), 7.88 (1H, s)

Compound 2-33

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.27 (3H, t, J=7 Hz), 2.6–2.7 (2H, m), 7.19 (1H, dt, J=8 Hz, 1 Hz), 7.3–7.5 (2H, m), 7.69 (1H, d, J=1.6 Hz), 7.85 (1H, d, J=1.6 Hz)

Compound 3-1

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 7.11 (2H, dd, J=7.7 Hz, 9.2 Hz), 7.39 (1H, d, J=2.5 Hz), 7.48 (1H, d, J=2.5 Hz), 11.9 (2H, brs)

Compound 3-2 (DBN salt)

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 1.8–1.9 (2H, m), 1.9–2.0 (2H, m), 2.76 (2H, t, J=7.9 Hz), 3.27 (2H, t, J=5.7), 3.35 (2H, t, J=5.7 Hz), 3.58 (2H, t, J=7.2 Hz), 6.69 (1H, d, J=1.6 Hz), 7.0–7.1 (1H, m), 7.07 (1H, d, J=1.6 Hz), 7.1–7.2 (2H, m), 10.35 (2H, brs)

Compound 3-3

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 7.05 (2H, t, J=8 Hz), 7.3–7.4 (1H, m), 7.40 (1H, d, J=2 Hz), 7.49 (1H, d, J=2 Hz), 11.94 (2H, brs)

Compound 3-4

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 7.15 (1H, t, J=7 Hz), 7.29 (2H, t, J=7 Hz), 7.38 (1H, d, J=2.4 Hz), 7.46 (2H, d, J=7 Hz), 7.49 (1H, d, J=2.4 Hz), 11.74 (brs)

Compound 3-5

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 7.2–7.3 (3H, m), 7.38 (1H, d, J=2.6 Hz), 7.4–7.5 (1H, m), 7.49 (1H, d, J=2.4 Hz), 12.5 (brs)

Compound 3-6

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 7.1–7.2 (2H, m), 7.2–7.4 (2H, m), 7.39 (1H, d, J=2.7 Hz), 7.50 (1H, d, J=2.4 Hz), 12.6 (brs)

Compound 3-7

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 2.11 (3H, s), 7.1–7.2 (4H, m), 7.3–7.4 (1H, m), 7.4–7.5 (1H, m), 12.5 (brs)

Compound 3-8

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 7.30 (1H, d, J=7.7 Hz), 7.37 (1H, d, J=2.4 Hz), 7.4–7.6 (2H, m), 7.64 (1H, t, J=7.5 Hz), 7.73 (1H, d, J=8.0 Hz)

Compound 3-12

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 7.11 (2H, t, J=8.8 Hz), 7.38 (1H, d, J=2.4 Hz), 7.4–7.5 (3H, m), 11.4 (brs), 12.3 (brs)

Compound 3-13 (DBU salt)

¹H-NMR δ (ppm; TMS): (DMSO-d6) 1.59–1.67 (6H, m), 1.87–1.94 (2H, m), 2.49–2.51 (2H, m), 3.23 (2H, t, J=5.6 Hz), 3.46 (2H, t, J=5.7 Hz), 3.52–3.56 (2H, m), 6.69 (1H, d, J=1.5 Hz), 7.09 (1H, d, J=1.5 Hz), 7.15–7.20 (1H, m), 7.35 (2H, d, J=8.0 Hz), 9.5 (brs), 10.3 (brs)

Compound 3-15

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 7.04 (1H, dt, J=2.4 Hz,8.5 Hz), 7.16 (1H, dt, J=2.6 Hz,9.7 Hz), 7.34 (1H, dt, J=7.0 Hz,8.5 Hz), 7.40 (1H, d, J=2.4Hz,) 7.49 (1H, d, J=2.4 Hz)

Compound 3-16

¹H-NMR δ (ppm; TMS) (DMSO-d₆) 7.3–7.4 (2H, m), 7.52 (1H, d, J=2.6 Hz), 7.59 (2H, dt, J=1.7 Hz)

Compound 4-5

¹H-NMR δ (ppm; TMS): (DMSO-d₆) 2.03 (3H, s), 7.2–7.3 (1H, m), 7.4–7.5 (2H, m), 7.51 (1H, d, J=2.4 Hz), 7.59 (1H, d, J=2.4 Hz), 12.90 (1H, brs)

Compound 4-6

¹H-NMR δ (ppm; TMS): (CDCl₃) 1.29 (3H, t, J=7 Hz), 2.5–2.6 (2H, m), 7.0–7.2 (2H, m), 7.3–7.4 (2H, m), 7.67 (1H, d, J=2.3 Hz)

Next, the formulation examples are given below. Part represents part by weight and the present compounds are referred to the numbers described in the above table.

FORMULATION EXAMPLE 1

Fifty parts of each of Compounds 1–637, 3 parts of calcium ligninsulfonate, 2 parts of magnesium laurylsulfate and 45 parts of synthetic hydrated silicon dioxide are well pulverized and mixed to give each of wettable powders.

FORMULATION EXAMPLE 2

Twenty parts of each of Compounds 1–637 and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of aqueous solution containing 2% by weight of polyvinyl alcohol, and finely pulverized with wet pulverizing method. Forty parts of aqueous solution containing 0.05% by weight of xanthan gum and 0.1% by weight of aluminum magnesium silicate are added thereto, and further 10 parts of propylene glycol were added and stirred to give each of flowable formulations.

FORMULATION EXAMPLE 3

Two parts of each of Compounds 1–637, 88 parts of kaolin clay and 10 parts of talc are well pulverized and mixed to give each of dusts.

FORMULATION EXAMPLE 4

Five parts of each of Compounds 1–637, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene are well mixed to give each of emulsifiable concentrate.

FORMULATION EXAMPLE 5

Two parts of each of Compounds 1–637, one part of synthetic hydrated silicon dioxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are well pulverized and mixed. Water is added thereto and well kneaded to give each of granules.

FORMULATION EXAMPLE 6

Ten parts of each of Compounds 1–637, 35 parts of white carbon containing 50% by weight of polyoxyethylene alkyl ether sulfate and 55 parts of water are mixed, and finely pulverized with wet pulverizing method to give each of flowable formulations.

The following test examples show that the present compounds are useful for controlling plant diseases. The present compounds are referred to the numbers described in the above table.

The control effect of the present compound was evaluated by visually observing the area of a lesion on a plant under test in investigation and comparing the area of a lesion in a non-treatment group and the area of a lesion in a group treated with the present compound.

TEST EXAMPLE 1 Preventive Efficacy Against Botrytis cinerea on Cucumber

Sand loam was compacted in plastic pots, cucumbers (Ochiai Aonagafushinari) were seeded and grown in a greenhouse for 10 days. Then, Compounds 7, 8, 9, 21, 29, 49, 50, 52, 53, 54, 55, 63, 65, 71, 72, 73, 81, 83, 85, 89, 161, 180, 187, 226, 228, 233, 251, 255, 259, 267, 283, 285, 287, 295, 428, 449, 521 and 535 were formulated into flowable formulations according to Formulation Example 6, then, diluted with water to provide prescribed concentration (500 ppm), and these were sprayed over the foliage so as to give sufficient adhesion on the surface of cucumber cotyledons. After spraying, the plants were air-dried, and PDA medium containing spores of Botrytis cinerea were attached on cucumber cotyledons. After the inoculation, the cucumbers were placed in a humid condition at 12° C. for 4 days, and the control effect was examined. The results showed that areas of lesions on the plants of the groups treated with the present compounds were not greater than 30% of areas of lesions on those of the untreated groups.

TEST EXAMPLE 2 Preventive Efficacy Against Sphaerotheca fuliginea on Cucumber

Sand loam was compacted in plastic pots, cucumbers (Ochiai Aonagafushinari) were seeded and grown in a greenhouse for 12 days. Then, Compounds 1, 4, 7, 8, 20, 52, 55, 76, 81, 83, 161 and 449 were formulated into flowable formulations according to Formulation Example 6, then, diluted with water to provide prescribed concentration (500 ppm), and these were sprayed over the foliage so as to give sufficient adhesion on the surface of cucumber leaves. After spraying, the plants were air-dried, and inoculated with spores of Sphaerotheca fuliginea. After the inoculation, the cucumbers were placed at 23° C. for 12 days, and the control effect was examined. The results showed that areas of lesions on the plants of the groups treated with the present compounds were not greater than 30% of areas of lesions on those of the untreated groups.

For the reference, the compound of Example 12 on page 12 of JP2001-19693A (hereinafter referred to as Reference Compound A) and Compound 182 of the present invention were tested.

TEST EXAMPLE 3 Preventive Efficacy Against Botrytis cinerea on Cucumber

Sand loam was compacted in plastic pots, cucumbers (Ochiai Aonagafushinari) were seeded and grown in a greenhouse for 10 days. Then, each of Reference Compound A and Compound 182 was formulated into a flowable formulation according to Formulation Example 6, then, diluted with water to provide prescribed concentration (500 ppm), and sprayed over the foliage so as to give sufficient adhesion on the surface of cucumber cotyledons. After spraying, the plants were air-dried, and PDA medium containing spores of Botrytis cinerea were attached on cucumber cotyledons. After the inoculation, the cucumbers were placed in a humid condition at 12° C. for 4 days, and the control effect was examined. As a result, areas of lesions on the plant treated with Reference Compound A were in the range of 75% to 100% on those of the untreated groups, on the other hand, areas of lesions on the plant treated with Compound 182 was not greater than 1% of areas of lesions on those of the untreated groups.

TEST EXAMPLE 4 Preventive Efficacy Against Sphaerotheca fuliginea on Cucumber

Sand loam was compacted in plastic pots, cucumbers (Ochiai Aonagafushinari) were seeded and grown in a greenhouse for 12 days. Then, each of Reference Compound A and Compound 182 was formulated into flowable formulations according to Formulation Example 6, then, diluted with water to provide prescribed concentration (500 ppm), and sprayed over the foliage so as to give sufficient adhesion on the surface of cucumber leaves. After spraying, the plants were air-dried, and inoculated with spores of Sphaerotheca fuliginea. After the inoculation, the cucumbers were placed at 23° C. for 12 days, and the control effect was examined. As a result, areas of lesions on the plant treated with Reference Compound A were in the range of 75% to 100% on those of the untreated groups, on the other hand, areas of lesions on the plant treated with Compound 182 was not greater than 1% of infested areas on those of the untreated groups.

INDUSTRIAL APPLICABILITY

It can be controlled plant diseases by using the present compound. 

1. An imidazo[1,2-a]pyrimidine given by the following formula [I]:

[wherein R¹ represents a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; phenyl group or phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring; 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group; R² represents a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; phenyl group or phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring; 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group; amino group optionally substituted by one or more selected from the group consisting of C1–C6 alkyl group, phenly group and benzyl group (said phenly group and benzyl group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C3 haloalkyl group and halogen atoms on the benzene ring); C1–C4 alkoxy group; phenoxy group; benzyloxy group; or R¹ and R² together with the nitrogen atom bonded with R¹ and R² represent 3–8 membered heterocyclic group (said heterocyclic group may be substituted by C1–C4 alkylene group or C2–C4 alkenylene group to represent polycyclic heterocyclic group, and substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group); R³ represents a halogen atom or C1–C4 alkyl group; Ar represents a phenyl group optionally substituted by one or more selected from the group consisting of halogen atoms, C1–C4 alkyl group, C1–C4 alkoxy group and C1–C3 haloalkyl group].
 2. The imidazo[1,2-a]pyrimidine according to claim 1, wherein R¹ is a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; phenyl group or phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring; 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group; R² is a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; phenyl group or phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring; 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group; amino group optionally substituted by one or more selected from the group consisting of C1–C6 alkyl group, pheny group and benzyl group (said pheny group and benzyl group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C3 haloalkyl group and halogen atoms on the benzene ring); C1–C4 alkoxy group; phenoxy group; benzyloxy group; or R¹ and R² together with the nitrogen atom bonded with R¹ and R² are 3–8 membered heterocyclic group (said heterocyclic group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group) in the formula [I].
 3. The imidazo[1,2-a]pyrimidine according to claim 1, wherein R¹ and R² are independently a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; phenyl group or phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring; 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group; or R¹ and R² together with the nitrogen atom bonded with R¹ and R² are 3–8 membered heterocyclic group (said heterocyclic group may be substituted by C1–C4 alkylene group or C2–C4 alkenylene group to be polycyclic heterocyclic group, and substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group) in the formula [I].
 4. The imidazo[1,2-a]pyrimidine according to claim 1, wherein R¹ and R² are independently a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; phenyl group or phenyl C1–C2 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C3 haloalkoxy group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group on the benzene ring; 5 or 6 membered heterocyclic group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, halogen atoms, nitro group, cyano group and C2–C5 alkoxycarbonyl group; or R¹ and R² together with the nitrogen atom bonded with R¹ and R² are 3–8 membered heterocyclic group (said heterocyclic group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group) in the formula [I].
 5. The imidazo[1,2-a]pyrimidine according to claim 1, wherein R¹ and R² are independently a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; or R¹ and R² together with the nitrogen atom bonded with R¹ and R² are 3–8 membered heterocyclic group (said heterocyclic group may be substituted by C1–C4 alkylene group or C2–C4 alkenylene group to be polycyclic heterocyclic group, and substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group) in the formula [I].
 6. The imidazo[1,2-a]pyrimidine according to claim 1, wherein R¹ and R² are independently a hydrogen atom; C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; or R¹ and R² together with the nitrogen atom bonded with R¹ and R² are 3–8 membered heterocyclic group (said heterocyclic group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group) in the formula [I].
 7. The imidazo[1,2-a]pyrimidine according to claim 1, wherein R¹ and R² are independently a C1–C6 alkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkoxy group, C2–C8 dialkylamino group, C1–C4 alkylthio group, C2–C5 alkoxycarbonyl group, cyano group and halogen atoms; C3–C6 alkenyl group optionally substituted by a halogen atom or atoms; C3–C6 alkynyl group optionally substituted by a halogen atom or atoms; C3–C8 cycloalkyl group optionally substituted by one or more selected from the group consisting of C1–C4 alkyl group and halogen atoms; or R¹ and R² together with the nitrogen atom bonded with R¹ and R² are 3–8 membered heterocyclic group (said heterocyclic group may be substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group) in the formula [I].
 8. The imidazo[1,2-a]pyrimidine according to claim 1, wherein R¹ and R² together with the nitrogen atom bonded with R¹ and R² are 3–8 membered heterocyclic group (said heterocyclic group may be substituted by C1–C4 alkylene group or C2–C4 alkenylene group to be polycyclic heterocyclic group, and substituted by one or more selected from the group consisting of C1–C4 alkyl group, C1–C4 alkoxy group, C1–C4 alkylthio group, C1–C3 haloalkyl group, C1–C4 acyl group, halogen atoms, hydroxy group, nitro group, cyano group and C2–C5 alkoxycarbonyl group) in the formula [I].
 9. The imidazo[1,2-a]pyrimidine according to claim 8, wherein the 3–8 membered heterocyclic group represented by R¹ and R² together with the nitrogen atom bonded with R¹ and R² in the formula [I] is pyrrolidin-1-yl group, piperidin-1-yl group, morpholin-4-yl group, thiomorpholin-4-yl group or hexamethylene-1-yl group.
 10. The imidazo[1,2-a]pyrimidine according to claim 1, wherein the Ar in the formula [I] is a phenyl group substituted by a halogen atom or atoms at one or more of 2-, 4- and 6-position.
 11. The imidazo[1,2-a]pyrimidine according to claim 1, wherein the Ar in the formula [I] is a phenyl group substituted by fluorine atoms or chlorine atoms at two or more of 2-, 4- or 6-position and unsubstituted at 3- and 5-position.
 12. The imidazo[1,2-a]pyrimidine according to claim 1, wherein the Ar in the formula [I] is a 2,6-difluorophenyl group, 2,4,6-trifluorophenyl group, 4-chloro-2,6-difluorophenyl group, 2-chloro-6-fluorophenyl group, 2-chloro-4,6-difluorophenyl group or 2,4-dichloro-6-fluorophenyl group.
 13. The imidazo[1,2-a]pyrimidine according to claim 1, wherein R³ is a chlorine atom or methyl group; and Ar is a 2,6-difluorophenyl group, 2,4,6-trifluorophenyl group, 4-chloro-2,6-difluorophenyl group, 2-chloro-6-fluorophenyl group, 2-chloro-4,6-difluorophenyl group or 2,4-dichloro-6-fluorophenyl group in the formula [I].
 14. A fungicidal composition comprising the imidazo[1,2-a]pyrimidine described in claim 1 as an active ingredient.
 15. A method for controlling fungal plant diseases which comprise applying the imidazo[1,2-a]pyrimidine described in claim 1 to a plant or soil for cultivating the plant.
 16. An imidazo[1,2-a]pyrimidine given by the following formula [II]:

[wherein X represents a halogen atom; R³ represents a halogen atom or C1–C4 alkyl group; and Ar represents a phenyl group optionally substituted by a halogen atoms, or atoms at one or more of 2-, 4- or 6-position.
 17. The imidazo[1,2-a]pyrimidine according to claim 16, wherein the Ar in the formula [II] is a 2,6-difluorophenyl group, 2,4,6-trifluorophenyl group, 4-chloro-2,6-difluorophenyl group, 2-chloro-6-fluorophenyl group, 2-chloro-4,6-difluorophenyl group or 2,4-dichloro-6-fluorophenyl group.
 18. An imidazo[1,2-a]pyrimidine given by the following formula [III]:

[wherein Ar represents a phenyl group optionally substituted by one or more selected from the group consisting of halogen atoms, C1–C4 alkyl group, C1–C4 alkoxy group and C1–C3 haloalkyl group].
 19. The imidazo[1,2-a]pyrimidine according to claim 18, wherein the Ar in the formula [III] is a phenyl group substituted by a halogen atom or atoms at one or more of 2-, 4- or 6-position.
 20. The imidazo[1,2-a]pyrimidine according to claim 18, wherein the Ar in the formula [III] is a 2,6-difluorophenyl group, 2,4,6-trifluorophenyl group, 4-chloro-2,6-difluorophenyl group, 2-chloro-6-fluorophenyl group, 2-chloro-4,6-difluorophenyl group or 2,4-dichloro-6-fluorophenyl group.
 21. An imidazo[1,2-a]pyrimidine given by the following formula [IV]:

[wherein R⁸ represents a C1–C4 alkyl group; and Ar represents a phenyl group optionally substituted by one or more selected from the group consisting of halogen atoms, C1–C4 alkyl group, C1–C4 alkoxy group and C1–C3 haloalkyl group].
 22. The imidazo[1,2-a]pyrimidine according to claim 21, wherein the Ar in the formula [IV] is a phenyl group substituted by a halogen atom or atoms at one or more of 2-, 4- or 6-position.
 23. The imidazo[1,2-a]pyrimidine according to claim 21, wherein the Ar in the formula [IV] is a 2,6-difluorophenyl group, 2,4,6-trifluorophenyl group, 4-chloro-2,6-difluorophenyl group, 2-chloro-6-fluorophenyl group, 2-chloro-4,6-difluorophenyl group or 2,4-dichloro-6-fluorophenyl group. 